methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside

Base Information

• Chemical Name: methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside
• CAS No.: 114217-36-6
• Molecular Formula: C₂₆H₃₆O₆Si
• Molecular Weight: 472.654
• Mol file: 114217-36-6.mol

Synonyms:methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside

Chemical Property of methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside

There total 2 articles about methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-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: 93.0%

tert-butylchlorodiphenylsilane (58479-61-1) + methyl 3,4-O-isopropylidene-α-D-galactopyranoside (40269-01-0) → methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside (114217-36-6)

Guidance literature:

With 4-methylpyridine-1-oxide; In dichloromethane; at 20 ℃; regioselective reaction; Molecular sieve;

DOI:10.1016/j.tetlet.2015.12.114

Reference yield: 90.0%

Trifluoro-methanesulfonic acid (3aS,4R,6S,7R,7aS)-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester (114217-37-7) + 2,2-dimethoxy-propane (77-76-9) → methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside (114217-36-6)

Guidance literature:

With camphor-10-sulfonic acid; In acetone;

DOI:10.1016/S0040-4039(00)96272-5

Reference yield: 90.0%

2-(((2R,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide + methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside (114217-36-6) → (((3aS,4R,6S,7R,7aS)-7-(((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl)oxy)-6-methoxy-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)methoxy)(tert-butyl)diphenylsilane

Guidance literature:

With C₅₀H₅₅F₉N₆O₄S₂; at 40 ℃; for 18h; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/jacs.0c00335

upstream raw materials:

Trifluoro-methanesulfonic acid (3aS,4R,6S,7R,7aS)-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

2,2-dimethoxy-propane

tert-butylchlorodiphenylsilane

methyl 3,4-O-isopropylidene-α-D-galactopyranoside

Downstream raw materials:

Trifluoro-methanesulfonic acid (3aS,4R,6S,7R,7aS)-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

methyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-β-D-galactopyranoside

methyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside

methyl (2,3-di-O-acetyl-3-C-(benzyloxymethyl)β-D-erythrofuranosyl)-(1->2)-6-O-(tert-butyldiphenyl)silyl-3,4-O-isopropylidene-α-D-galactopyranoside