(2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol

Base Information

• Chemical Name: (2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol
• CAS No.: 114079-08-2
• Molecular Formula: C₅₆H₉₃NO₆
• Molecular Weight: 876.358

Synonyms:(2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol

Chemical Property of (2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol

Chemical Property:

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Technology Process of (2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol

There total 1 articles about (2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol 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%

(2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoyl-1-O-triphenylmethyl-2-amino-1,3,4-octadecanetriol (129779-81-3) → (2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol (114079-08-2)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; dichloromethane; for 16h; Ambient temperature;

Reference yield: 71.0%

phenyl 2-O-benzoyl-4-O-tert-butyldimethylsilyl-3,6-di-O-4-methoxybenzyl-1-thio-β-D-glucopyranoside (1374564-15-4) + (2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol (114079-08-2) → (2-O-benzoyl-4-O-tert-butyldimethylsilyl-3,6-di-O-p-methoxybenzyl-β-D-glucopyranosyl)-(1 → 1)-(2S,3S,4R)-3,4-di-O-benzoyl-2-tetracosanamido-1,3,4-octadecanetriol

Guidance literature:

phenyl 2-O-benzoyl-4-O-tert-butyldimethylsilyl-3,6-di-O-4-methoxybenzyl-1-thio-β-D-glucopyranoside; (2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol; With N-iodo-succinimide; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 1h; Molecular sieve; Inert atmosphere;

DOI:10.1039/c5ob01744k

Reference yield: 45.0%

(2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol (114079-08-2) + O-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate (132287-70-8) → O-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->1)-(2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoylsphinganine (132287-77-5,132341-48-1)

Guidance literature:

With 3 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1271/bbb1961.54.2931

upstream raw materials:

(2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoyl-1-O-triphenylmethyl-2-amino-1,3,4-octadecanetriol

Downstream raw materials:

O-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->1)-(2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoylsphinganine

O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->1)-(2S,3S,4R)-3,4-di-O-benzoyl-N-tetracosanoylsphinganine

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