(+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)cyclohexyl methanesulfonate

Base Information

• Chemical Name: (+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)cyclohexyl methanesulfonate
• CAS No.: 950170-55-5
• Molecular Formula: C₃₅H₃₇N₃O₇S
• Molecular Weight: 643.761
• Mol file: 950170-55-5.mol

Synonyms:(+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)cyclohexyl methanesulfonate

Chemical Property of (+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)cyclohexyl methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)cyclohexyl methanesulfonate

There total 6 articles about (+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)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: 81.0%

(+)-(1R,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol (864948-63-0) + methanesulfonyl chloride (124-63-0) → (+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)cyclohexyl methanesulfonate (950170-55-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 26h;

DOI:10.1016/j.carres.2007.04.024

Reference yield:

(+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol (4381-96-8,6216-24-6,25348-63-4,80226-74-0,109526-05-8,123354-99-4,123355-00-0,123355-01-1,129829-60-3,129829-61-4,133319-96-7,143615-78-5,143615-79-6) → (+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)cyclohexyl methanesulfonate (950170-55-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 43 percent / tetrahexylammonium bromide; aq. NaOH; chiral diphosphine C44H40N2O2P2 / [η³-allylPdCl]2 / CH2Cl2 / 30 °C

2.1: 99 percent / NaOMe / methanol / 24 h / 20 °C

3.1: 88 percent / m-CPBA / methanol / 20 °C

4.1: NaH / dimethylformamide / 0.5 h / 30 °C

4.2: 68 percent / dimethylformamide / 30 °C

5.1: 61 percent / LiClO₄; NaN₃ / acetonitrile / 24 h / Heating

6.1: 81 percent / Et₃N / tetrahydrofuran / 26 h / 20 °C

With sodium hydroxide; sodium azide; sodium methylate; lithium perchlorate; tetrahexylammonium bromide; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; [η³-allylPdCl]2; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.carres.2007.04.024

Reference yield:

(+)-(1R,2R,3S,4S,5R,6S)-2,3,4,5-tetraol-7-oxabicyclo[4.1.0]heptane (6090-95-5,6705-47-1,7115-27-7,23559-36-6,33800-41-8,57090-00-3,80736-37-4,80736-38-5,101312-05-4,145107-29-5,145107-31-9,133319-97-8) → (+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)cyclohexyl methanesulfonate (950170-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 0.5 h / 30 °C

1.2: 68 percent / dimethylformamide / 30 °C

2.1: 61 percent / LiClO₄; NaN₃ / acetonitrile / 24 h / Heating

3.1: 81 percent / Et₃N / tetrahydrofuran / 26 h / 20 °C

With sodium azide; lithium perchlorate; sodium hydride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.carres.2007.04.024

upstream raw materials:

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

methanesulfonyl chloride

(+)-(1R,2R,3S,4S,5R,6S)-2,3,4,5-tetraol-7-oxabicyclo[4.1.0]heptane

(1S,2R,3R,4S)-1,2,3,4,tetrahydroxy-5-cyclohexene

Downstream raw materials:

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

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