1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside

Base Information

• Chemical Name: 1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside
• CAS No.: 214468-40-3
• Molecular Formula: C₂₅H₃₂O₅Si
• Molecular Weight: 440.612
• Mol file: 214468-40-3.mol

Synonyms:1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside

Chemical Property of 1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside

There total 1 articles about 1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-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:

phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-D-galactal (137792-66-6) → 1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside (214468-40-3)

Guidance literature:

With 3,3-dimethyldioxirane; In dichloromethane; acetone; at 0 ℃; for 1h;

DOI:10.1021/ja980489k DOI:10.1016/S0040-4020(98)83057-3

Reference yield: 30.0%

1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside (214468-40-3) + (5R)-Nα-[(fluoren-9-yl)methoxycarbonyl]-Nε-benzyloxycarbonyl-5-hydroxy-L-lysine allyl ester (254757-67-0) → (3aS,4R,6R,7R,7aR)-6-Allyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol + [(3S,6R)-6-(Benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-yl]-carbamic acid 9H-fluoren-9-ylmethyl ester + (5R)-Nα-(fluoren-9-ylmethoxycarbonyl)-Nε-benzyloxycarbonyl-5-O-(6-O-tert-butyldimethylphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranosyl)-5-hydroxy-L-lysine allyl ester + (5R)-Nα-(fluoren-9-ylmethoxycarbonyl)-Nε-benzyloxycarbonyl-5-O-(6-O-tert-butyldimethylphenylsilyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-5-hydroxy-L-lysine allyl ester

Guidance literature:

With AW-300 MS; zinc(II) chloride; In tetrahydrofuran; diethyl ether; at -50 - 20 ℃; for 16h;

DOI:10.1021/jo990853d

Reference yield:

1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside (214468-40-3) → (S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid

Guidance literature:

Multi-step reaction with 2 steps

1: ZnCl₂, molecular sieves AW-300 / tetrahydrofuran; diethyl ether / 18 h / -50 - 20 °C

2: 93 percent / H₂ / Pd/C / ethyl acetate / 3 h / Ambient temperature

With 3 A molecular sieve; hydrogen; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate;

DOI:10.1016/S0040-4020(98)83057-3

upstream raw materials:

phenyl 6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-D-galactal

Downstream raw materials:

(S)-5-[(3aS,4R,6R,7R,7aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid benzyl ester

(2S,5R)-6-tert-Butoxycarbonylamino-5-[(3aS,4R,6R,7R,7aR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid benzyl ester