(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside

Base Information

Chemical Name:(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside
CAS No.:1215176-83-2
Molecular Formula:C₅₄H₈₂O₉Si
Molecular Weight:903.325
Hs Code.:

Synonyms:(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside

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Chemical Property of (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside

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Technology Process of (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside

There total 4 articles about (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside 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: 46.0%

: 1201598-10-8
O-(2,3-di-O-benzyl-4,6-O-benzylidene-D-galactopyranosyl) trichloroacetimidate

: 1215176-80-9
(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecan-1-ol

: 1242144-15-5
(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

: 1215176-83-2
(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside

Guidance literature:: With silver trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 2.5h; Molecular sieve;
DOI:10.1016/j.carres.2010.05.003

Reference yield:

: 1215176-80-9
(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecan-1-ol

: 303752-87-6
O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate

: 1242144-15-5
(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

: 1215176-83-2
(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside

Guidance literature:: (2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecan-1-ol; O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieves 4 ?;

With silver trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 2.5h;

Reference yield:

: 1215176-72-9
(2S,3S,4R,5EZ)-1-tert-butyldimethylsilyloxy-3,4-O-isopropylidene-5-octadecen-2-ol

: 1242144-15-5
(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

: 1215176-83-2
(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: hydrogen / palladium hydroxide on carbon / ethyl acetate / 1 h / 20 °C

2.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C

3.1: pyridine; pyridine hydrofluoride / tetrahydrofuran / 4 h / 0 - 20 °C

4.1: dichloromethane / 0.5 h / 20 °C / Molecular sieves 4 ?

4.2: 2.5 h / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; pyridine hydrofluoride; hydrogen; palladium hydroxide on carbon; In tetrahydrofuran; dichloromethane; ethyl acetate;