DT A NN-CHEMENTITY solution IN-OF of OSCAR-CM tetraol CD 113 -LRB- ( CD 74 NN-MASS mg COMMA , CD 0.30 NN-AMOUNT mmol -RRB- ) VBD was VBN taken RP up IN-IN in JJ-CHEM dry OSCAR-CM DMF -LRB- ( CD 2 NN-VOL mL -RRB- ) CC and VB-COOL cooled TO to CD 0 NN-TEMP ºC STOP . OSCAR-CM Imidazole -LRB- ( CD 40 NN-MASS mg COMMA , CD 0.60 NN-AMOUNT mmol -RRB- ) VBD was VB-ADD added CC and VBN allowed TO to VB-DISSOLVE dissolve VBN followed IN-BY by DT a NN-CHEMENTITY solution IN-OF of OSCAR-CM TIPSCl -LRB- ( CD 0.08 NN-VOL mL COMMA , CD 0.36 NN-AMOUNT mmol -RRB- ) CC and OSCAR-CM DMAP -LRB- ( CD 2.0 NN-MASS mg COMMA , CD 20 OSCAR-CM ?mol -RRB- ) IN-IN in OSCAR-CM DMF -LRB- ( CD 1 NN-VOL mL -RRB- ) STOP . DT-THE The JJ-CHEM reaction NN-CHEMENTITY mixture VBD was VB-HEAT heated IN at CD 50 NN-TEMP ºC IN-FOR for CD 18 NN-TIME hrs RB-CONJ then VB-QUENCH quenched IN-BY by NN-ADD addition IN-OF of JJ-CHEM saturated OSCAR-CM NH4Cl -LRB- ( JJ-CHEM aq -RRB- ) -LRB- ( CD 2 NN-VOL mL -RRB- ) CC and VB-DILUTE diluted IN-WITH with -LRB- ( CD 3 NN-VOL mL -RRB- ) STOP . DT-THE The OSCAR-CJ aqueous NN-CHEMENTITY layer VBD was VB-EXTRACT extracted IN-WITH with OSCAR-CM EtOAc -LRB- ( CD 3 NN x CD 10 NN-VOL mL -RRB- ) CC and DT-THE the JJ-CHEM combined JJ-CHEM organic NN-CHEMENTITY layers VB-WASH washed IN-WITH with CD 10 NN-PERCENT % OSCAR-CJ aqueous OSCAR-CM LiCl -LRB- ( CD 5 NN x CD 10 NN-VOL mL -RRB- ) COMMA , JJ-CHEM saturated OSCAR-CM brine -LRB- ( CD 5 NN-VOL mL -RRB- ) COMMA , VB-DRY dried -LRB- ( OSCAR-CM MgSO4 -RRB- ) COMMA , VB-FILTER filtered CC and VB-CONCENTRATE concentrated IN-IN in NN-VACUUM vacuo TO to VB-YIELD give DT-THE the JJ-CHEM crude NN-CHEMENTITY product IN-AS as DT a JJ yellow NN-STATE oil STOP . NN-FLASH Flash NN-CHROMATOGRAPHY chromatography VB-USE using OSCAR-CM CH2Cl2 DASH / OSCAR-CM MeOH -LRB- ( CD 98 COLON : CD 2 -RRB- ) VB-YIELD afforded DT-THE the JJ-COMPOUND title NN-CHEMENTITY compound CD 115 IN-AS as DT a JJ clear NN-STATE oil -LRB- ( CD 101 NN-MASS mg COMMA , CD 83 NN-PERCENT % -RRB- ) STOP . OSCAR-CM 2-((2R,3R,4R,5R,6R)-3,4-Bis(4-methoxybenzyloxy)-6-((R)-1-(4-methoxybenzyloxy)-2-(methylallyl)-5-methyltetrahydro-2H-pyran-2-yl)ethoxy)(tert-butyl)dimethylsilane CD 116 DT A NN-CHEMENTITY solution IN-OF of OSCAR-CM triol CD 114 -LRB- ( CD 60 NN-MASS mg COMMA , CD 0.17 NN-AMOUNT mmol -RRB- ) IN-IN in JJ-CHEM dry OSCAR-CM DMF -LRB- ( CD 2 NN-VOL mL -RRB- ) VBD was VB-COOL cooled TO to CD 0 NN-TEMP ºC. -LRB- ( CD 41 NN-MASS mg COMMA , CD 1.0 NN-AMOUNT mmol -RRB- ) VBD was VB-ADD added CC and DT-THE the NN-CHEMENTITY suspension VBD was VBN allowed TO to VB-HEAT warm TO to NN-TEMP room NN-TEMP temperature STOP . IN-AFTER After CD 1 NN-TIME h COMMA , OSCAR-CM PMBBr -LRB- ( CD 0.15 NN-VOL mL COMMA , CD 1.0 NN-AMOUNT mmol -RRB- ) CC and OSCAR-CM TBAI -LRB- ( CD 11 NN-MASS mg COMMA , CD 30 VBD ?mol)were VB-ADD added RB sequentially CC and DT-THE the JJ-CHEM reaction NN-CHEMENTITY mixture VBD was VB-STIR stirred IN-FOR for CD 18 NN-TIME h IN at JJ ambient NN-TEMP temperature STOP . DT-THE The NN-CHEMENTITY reaction VBD was RB-CONJ then VB-COOL cooled TO to CD 0 NN-TEMP ºC CC and VB-QUENCH quenched IN-BY by NN-ADD addition IN-OF of JJ-CHEM saturated OSCAR-CM NH4Cl -LRB- ( JJ-CHEM aq -RRB- ) -LRB- ( CD 5 NN-VOL mL -RRB- ) CC and VB-DILUTE diluted IN-WITH with -LRB- ( CD 5 NN-VOL mL -RRB- ) STOP . DT-THE The OSCAR-CJ aqueous NN-CHEMENTITY layer VBD was VB-EXTRACT extracted IN-WITH with OSCAR-CM EtOAc -LRB- ( CD 3 NN x CD 30 NN-VOL mL -RRB- ) CC and DT-THE the JJ-CHEM combined JJ-CHEM organic NN-CHEMENTITY layers VB-WASH washed IN-WITH with CD 10 NN-PERCENT % OSCAR-CJ aqueous OSCAR-CM LiCl -LRB- ( CD 3 NN x CD 30 NN-VOL mL -RRB- ) COMMA , JJ-CHEM saturated OSCAR-CM brine -LRB- ( CD 30 NN-VOL mL -RRB- ) COMMA , VB-DRY dried -LRB- ( OSCAR-CM MgSO4 -RRB- ) CC and VB-CONCENTRATE concentrated IN-UNDER under JJ reduced NN-PRESSURE pressure TO to VB-YIELD give DT-THE the JJ-CHEM crude NN-CHEMENTITY product IN-AS as DT a JJ yellow NN-STATE oil STOP . NN-FLASH Flash NN-CHROMATOGRAPHY chromatography IN @ VB-USE using OSCAR-CM petrol/EtOAc -LRB- ( CD 95 COLON : CD 5 -RRB- ) VB-YIELD afforded DT-THE the JJ-COMPOUND title NN-CHEMENTITY compound CD 116 IN-AS as DT a JJ white NN-STATE foam -LRB- ( CD 105 NN-MASS mg COMMA , CD 85 NN-PERCENT % -RRB- ) STOP .