(S)-2-Benzyloxycarbonylamino-3-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-3-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester
• CAS No.: 329365-88-0
• Molecular Formula: C₄₆H₄₉NO₁₀
• Molecular Weight: 775.896
• Mol file: 329365-88-0.mol

Synonyms:(S)-2-Benzyloxycarbonylamino-3-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

Chemical Property of (S)-2-Benzyloxycarbonylamino-3-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxycarbonylamino-3-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

There total 4 articles about (S)-2-Benzyloxycarbonylamino-3-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester 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: 95.0%

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose (80300-30-7) + (S)-2-Benzyloxycarbonylamino-3-trimethylsilanyloxy-propionic acid methyl ester (135195-50-5) → (S)-2-Benzyloxycarbonylamino-3-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester (329365-88-0)

Guidance literature:

silver perchlorate; tin(IV) chloride; In diethyl ether; toluene; at 0 ℃; for 18h;

Reference yield: 90.0%

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) + 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl N-trichloroacetylcarbamate (838888-66-7) → (S)-2-Benzyloxycarbonylamino-3-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester (329365-88-0)

Guidance literature:

With trimethylsilyl perchlorate; In diethyl ether; at 0 ℃; for 3h;

DOI:10.1016/j.tetlet.2005.11.027

Reference yield:

methyl 2-(benzyloxycarbonylamino)-3-hydroxypropanoate (14464-15-4) + 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) → (S)-2-Benzyloxycarbonylamino-3-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid methyl ester (329365-88-0)

Guidance literature:

With gold(III) chloride; In dichloromethane; at 35 - 39 ℃; for 0.166667h; diastereoselective reaction; Molecular sieve;

DOI:10.1002/ejoc.201500137

upstream raw materials:

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

(S)-2-Benzyloxycarbonylamino-3-trimethylsilanyloxy-propionic acid methyl ester

N-benzyloxycarbonyl-L-serine methyl ester

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl N-trichloroacetylcarbamate