3-β-cholestanyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 3-β-cholestanyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 121682-61-9
• Molecular Formula: C₅₆H₇₉NO₆
• Molecular Weight: 862.246
• Mol file: 121682-61-9.mol

Synonyms:3-β-cholestanyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of 3-β-cholestanyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-β-cholestanyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 3 articles about 3-β-cholestanyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside 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: 73.0%

cholestanol (17608-41-2) + 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl dimethylphosphinothioate (121123-46-4) → 3-β-cholestanyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (121682-61-9)

Guidance literature:

With 4 A molecular sieve; iodine; triphenylmethyl perchlorate; In benzene; Product distribution; various catalyst, reagent system;

DOI:10.1246/cl.1989.69

Reference yield: 50.0%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + cholestanol (17608-41-2) + N-Trimethylsilylacetamide (13435-12-6) → 3-β-cholestanyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (121682-61-9) + N-{(2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-[(3S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:

3,4,6-tri-O-benzyl-D-glucal; With 2,4,6-tri-tertbutylpyridine; 2,8-dimethyldibenzo[b,d]thiophene 5-oxide; trifluoromethanesulfonic acid anhydride; In dichloromethane; at -78 ℃; for 1h;

N-Trimethylsilylacetamide; With N,N-diethylaniline; In dichloromethane; at -78 ℃;

cholestanol; With camphor-10-sulfonic acid; In dichloromethane; at 23 ℃; for 24h;

DOI:10.1016/S0040-4039(03)00871-2

Reference yield:

2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose (4171-73-7) + cholestanol (17608-41-2) → 3-β-cholestanyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside + 3-β-cholestanyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (121682-61-9)

Guidance literature:

With boron trifluoride diethyl etherate; ytterbium(III) triflate; In dichloromethane; at 20 ℃; for 16h; Overall yield = 70 %;

DOI:10.3987/COM-14-S(K)4

upstream raw materials:

cholestanol

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl dimethylphosphinothioate

3,4,6-tri-O-benzyl-D-glucal

N-Trimethylsilylacetamide