benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)carbamate

Base Information

• Chemical Name: benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)carbamate
• CAS No.: 1316231-06-7
• Molecular Formula: C₄₃H₄₅NO₆
• Molecular Weight: 671.833
• Mol file: 1316231-06-7.mol

Synonyms:benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)carbamate

Chemical Property of benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)carbamate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)carbamate

There total 1 articles about benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)carbamate 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: 41.0%

(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine (124330-54-7) + benzyl chloroformate (501-53-1,94274-21-2) → benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)carbamate (1316231-06-7) + (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol (227930-76-9)

Guidance literature:

(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine; With N-Bromosuccinimide; In water; acetonitrile; at 20 ℃; for 15h; Inert atmosphere;

benzyl chloroformate; With sodium hydrogencarbonate; In methanol; chloroform; toluene; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1021/ja203574u

Reference yield: 95.0%

benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)carbamate (1316231-06-7) → validamine (32780-32-8)

Guidance literature:

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In methanol; water; ethyl acetate; for 20h; under 760.051 Torr;

DOI:10.1021/ja203574u

Reference yield: 66.0%

benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)carbamate (1316231-06-7) + acetic anhydride (108-24-7) → ((1R,2R,3S,4S,5S)-2,3,4-tris(benzyloxy)-5-(((benzyloxy)carbonyl)amino)cyclohexyl)methyl acetate (1316231-10-3)

Guidance literature:

With acetic acid; zinc(II) chloride; at 20 ℃; for 5h; regioselective reaction; Inert atmosphere;

DOI:10.1021/ja203574u

upstream raw materials:

(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine

benzyl chloroformate

Downstream raw materials:

benzyl ((1S,2S,3S,4R,5R)-2,3,4-Tris(benzyloxy)-5-(hydroxymethyl)cyclohexyl)carbamate

benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-(((bis(benzyloxy)phosphoryl)oxy)methyl)cyclohexyl)carbamate

validamine

(1S)-(+)-(1,2,4/3,5)-1-acetamido-2,3,4-triacetoxy-5-acetoxymethylcyclohexane