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

Base Information

• Chemical Name: (1R,2R,3S,4R,5S,6S)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate
• CAS No.: 868549-83-1
• Molecular Formula: C₄₀H₄₇NO₉S
• Molecular Weight: 717.88
• Mol file: 868549-83-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (1R,2R,3S,4R,5S,6S)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate 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: 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

Reference yield:

(1R,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakis(benzyloxy)cyclohexanol (1287225-25-5) → (1R,2R,3S,4R,5S,6S)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate (868549-83-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 0 - 20 °C

2: triethylamine / tetrahydrofuran / 5 h / 20 °C

With triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ml200098j

Reference yield:

(+)-(1R,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol (864948-63-0) → (1R,2R,3S,4R,5S,6S)-2,3,4,5-tetrakis(benzyloxy)-6-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate (868549-83-1)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C

2: triethylamine / dichloromethane / 0 - 20 °C

3: triethylamine / tetrahydrofuran / 5 h / 20 °C

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

DOI:10.1021/ml200098j

upstream raw materials:

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

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

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

methanesulfonyl chloride

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