3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-7,8-dideoxy-10,11:12,13-di-O-isopropylidene-β-L-glycero-D-gluco-D-gluco-tridecadialdo-7-en-1,5-pyranoside

Base Information

• Chemical Name: 3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-7,8-dideoxy-10,11:12,13-di-O-isopropylidene-β-L-glycero-D-gluco-D-gluco-tridecadialdo-7-en-1,5-pyranoside
• CAS No.: 389885-59-0
• Molecular Formula: C₈₄H₉₆O₁₇Si
• Molecular Weight: 1405.76

Synonyms:3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-7,8-dideoxy-10,11:12,13-di-O-isopropylidene-β-L-glycero-D-gluco-D-gluco-tridecadialdo-7-en-1,5-pyranoside

Chemical Property of 3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-7,8-dideoxy-10,11:12,13-di-O-isopropylidene-β-L-glycero-D-gluco-D-gluco-tridecadialdo-7-en-1,5-pyranoside

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Technology Process of 3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-7,8-dideoxy-10,11:12,13-di-O-isopropylidene-β-L-glycero-D-gluco-D-gluco-tridecadialdo-7-en-1,5-pyranoside

There total 1 articles about 3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-7,8-dideoxy-10,11:12,13-di-O-isopropylidene-β-L-glycero-D-gluco-D-gluco-tridecadialdo-7-en-1,5-pyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-7,8-dideoxy-10,11:12,13-di-O-isopropylidene-β-L-galacto-D-gluco-tridecadialdo-7-en-6-ulo-1,5-pyranoside → 3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-7,8-dideoxy-10,11:12,13-di-O-isopropylidene-β-L-glycero-D-gluco-D-gluco-tridecadialdo-7-en-1,5-pyranoside (389885-59-0)

Guidance literature:

With zinc borohydride; In diethyl ether; at 0 ℃;

DOI:10.1081/CAR-100105713

Reference yield: 88.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-7,8-dideoxy-10,11:12,13-di-O-isopropylidene-β-L-glycero-D-gluco-D-gluco-tridecadialdo-7-en-1,5-pyranoside (389885-59-0) → 3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-6-O-t-butyldimethylsilyl-7,8-dideoxy-10,11:12,13-di-O-isopropylidene-β-L-glycero-D-gluco-D-gluco-tridecadialdo-7-en-1,5-pyranoside

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 90 ℃; for 2h;

DOI:10.1081/CAR-100105713

Reference yield: 68.0%

3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-7,8-dideoxy-10,11:12,13-di-O-isopropylidene-β-L-glycero-D-gluco-D-gluco-tridecadialdo-7-en-1,5-pyranoside (389885-59-0) → 3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-D-glycero-α-D-glucopyranoside

Guidance literature:

3,4-di-O-benzyl-1-O-benzyloxymethyl-6-O-t-butyldiphenylsilyl-β-D-fructofuranosyl-(2-1)-(E)-2,3,4-tri-O-benzyl-7,8-dideoxy-10,11:12,13-di-O-isopropylidene-β-L-glycero-D-gluco-D-gluco-tridecadialdo-7-en-1,5-pyranoside; With ozone; In methanol; dichloromethane; at -78 ℃;

With sodium tetrahydroborate; In methanol; dichloromethane; at -78 - 20 ℃;

DOI:10.1081/CAR-100105713

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