2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl(1->1)(2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl(1->1)(2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol
• CAS No.: 381715-17-9
• Molecular Formula: C₆₄H₈₅NO₁₀
• Molecular Weight: 1028.38

Synonyms:2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl(1->1)(2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol

Chemical Property of 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl(1->1)(2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl(1->1)(2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol

There total 2 articles about 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl(1->1)(2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol 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: 42.0%

p-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (211678-08-9) + (2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol (381715-12-4) → 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl(1->1)(2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol (381715-17-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; dichloromethane; at -50 ℃;

DOI:10.1021/ja011382r

Reference yield:

N-(tert-butoxycarbonyl)-3-O-benzoyl-D-erythro-sphingosine (299172-59-1) → 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl(1->1)(2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol (381715-17-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / H₂ / Pd/C / ethanol

2: 42 percent / NIS; TfOH / CH₂Cl₂; diethyl ether / -50 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; hydrogen; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane;

DOI:10.1021/ja011382r

Reference yield:

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl(1->1)(2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol (381715-17-9) → [(1S,2R)-2-Hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadecyl]-carbamic acid tert-butyl ester (381715-20-4)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1021/ja011382r

upstream raw materials:

p-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside

(2S,3R)-3-O-benzoyl-2-(tert-butyloxycarbonylamino)-octadeca-1,3-diol

N-(tert-butoxycarbonyl)-3-O-benzoyl-D-erythro-sphingosine

Downstream raw materials:

[(1S,2R)-2-Hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadecyl]-carbamic acid tert-butyl ester

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