N-((1R,2S,3R,4R,5S,6R)-2,3,4,5-tetrabenzyloxy-6-hydroxycyclohexyl)carbamic acid tert-butyl ester

Base Information

• Chemical Name: N-((1R,2S,3R,4R,5S,6R)-2,3,4,5-tetrabenzyloxy-6-hydroxycyclohexyl)carbamic acid tert-butyl ester
• CAS No.: 1310554-91-6
• Molecular Formula: C₃₉H₄₅NO₇
• Molecular Weight: 639.789
• Mol file: 1310554-91-6.mol

Synonyms:N-((1R,2S,3R,4R,5S,6R)-2,3,4,5-tetrabenzyloxy-6-hydroxycyclohexyl)carbamic acid tert-butyl ester

Chemical Property of N-((1R,2S,3R,4R,5S,6R)-2,3,4,5-tetrabenzyloxy-6-hydroxycyclohexyl)carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((1R,2S,3R,4R,5S,6R)-2,3,4,5-tetrabenzyloxy-6-hydroxycyclohexyl)carbamic acid tert-butyl ester

There total 2 articles about N-((1R,2S,3R,4R,5S,6R)-2,3,4,5-tetrabenzyloxy-6-hydroxycyclohexyl)carbamic acid tert-butyl 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: 82.0%

di-tert-butyl dicarbonate (24424-99-5) + (1R,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakis(benzyloxy)cyclohexanol (1287225-25-5) → N-((1R,2S,3R,4R,5S,6R)-2,3,4,5-tetrabenzyloxy-6-hydroxycyclohexyl)carbamic acid tert-butyl ester (1310554-91-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ml200098j

Reference yield:

(+)-(1R,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol (864948-63-0) → N-((1R,2S,3R,4R,5S,6R)-2,3,4,5-tetrabenzyloxy-6-hydroxycyclohexyl)carbamic acid tert-butyl ester (1310554-91-6)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C

2: triethylamine / dichloromethane / 0 - 20 °C

With lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ml200098j

Reference yield: 63.0%

N-((1R,2S,3R,4R,5S,6R)-2,3,4,5-tetrabenzyloxy-6-hydroxycyclohexyl)carbamic acid tert-butyl ester (1310554-91-6) + methanesulfonyl chloride (124-63-0) → (1R,2R,3S,4R,5S,6S)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate (868549-83-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1021/ml200098j

upstream raw materials:

(+)-(1R,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol

di-tert-butyl dicarbonate

(1R,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakis(benzyloxy)cyclohexanol

Downstream raw materials:

N-((1R,2S,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakis(benzyloxy)cyclohexyl)carbamic acid tert-butyl ester

(1R,2S,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakis(benzyloxy)cyclohexanamine

(1R,2S,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakis(benzyloxy)-N-nonylcyclohexanamine

(1R,2R,3S,4R,5S,6S)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate