(2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-(2-O-methyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-1,3,4-octadecanetriol

Base Information

• Chemical Name: (2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-(2-O-methyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-1,3,4-octadecanetriol
• CAS No.: 676999-83-0
• Molecular Formula: C₆₀H₇₉N₃O₈
• Molecular Weight: 970.303

Synonyms:(2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-(2-O-methyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-1,3,4-octadecanetriol

Chemical Property of (2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-(2-O-methyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-1,3,4-octadecanetriol

Chemical Property:

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Technology Process of (2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-(2-O-methyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-1,3,4-octadecanetriol

There total 2 articles about (2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-(2-O-methyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-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: 69.0%

(2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-trityl-1,3,4-octadecanetriol (160280-67-1) + 3,4,6-tri-O-benzyl-2-O-methyl-D-galactopyranosyl acetate → (2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-(2-O-methyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-1,3,4-octadecanetriol (676999-83-0)

Guidance literature:

With silver perchlorate; tin(IV) chloride; In diethyl ether; toluene; for 14h;

DOI:10.1002/ejoc.200300512

Reference yield:

(2S,3S,4S)-2-azido-3,4-di-O-benzyl-octadecan-1,3,4-triol (202812-10-0) → (2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-(2-O-methyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-1,3,4-octadecanetriol (676999-83-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / 4-dimethylaminopyridine; pyridine / 12 h / 60 °C

2: 69 percent / SnCl₄; AgClO₄ / toluene; diethyl ether / 14 h

With pyridine; dmap; silver perchlorate; tin(IV) chloride; In diethyl ether; toluene; 2: Mukaiyama reaction;

DOI:10.1002/ejoc.200300512

Reference yield: 81.0%

(2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-(2-O-methyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-1,3,4-octadecanetriol (676999-83-0) → (2S,3S,4R)-2-amino-3,4-di-O-benzyl-1-O-(2-O-methyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-1,3,4-octadecanetriol (676999-84-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); triphenylstannane; In benzene; for 1h; Heating;

DOI:10.1002/ejoc.200300512

upstream raw materials:

(2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-trityl-1,3,4-octadecanetriol

(2S,3S,4S)-2-azido-3,4-di-O-benzyl-octadecan-1,3,4-triol

Downstream raw materials:

(2S,3S,4R)-2-amino-3,4-di-O-benzyl-1-O-(2-O-methyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-1,3,4-octadecanetriol

(2S,3S,4R)-2-docosanoylamino-3,4-di-O-benzyl-1-O-(2-O-methyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-1,3,4-octadecanetriol

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