(1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate

Base Information

• Chemical Name: (1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate
• CAS No.: 139402-99-6
• Molecular Formula: C₈H₁₆O₈S
• Molecular Weight: 272.276
• Mol file: 139402-99-6.mol

Synonyms:(1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate

Chemical Property of (1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate

There total 39 articles about (1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)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: 95.0%

Methanesulfonic acid (1R,2R,3R,4R,5R,6R)-2,3,4-tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexyl ester (128184-69-0,134680-61-8) → (1R,2R,3S,4R,5R,6R)-5-hydroxymethyl-6-methanesulfonyloxycyclohexane-1,2,3,4-tetraol (134651-20-0,136892-49-4,139402-99-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 25 ℃; for 6h; under 760 Torr;

DOI:10.1016/0008-6215(91)89017-A

Reference yield: 82.0%

Methanesulfonic acid (1R,2R,3R,4S,5R,6R)-2,3,4,5-tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl ester → (1R,2R,3S,4R,5R,6R)-5-hydroxymethyl-6-methanesulfonyloxycyclohexane-1,2,3,4-tetraol (134651-20-0,136892-49-4,139402-99-6)

Guidance literature:

With hydrogen; palladium dihydroxide; palladium on activated charcoal;

DOI:10.1021/jo00091a004

Reference yield: 80.0%

(1S,2R,3R,4R,5R,6S)-1,2,3-tribenzyloxy-6-methanesulfonyloxy-4-<(1-methylethyl)diethylsilyl>oxy-5-<<(1-methylethyl)diethylsilyl>oxy>methylcyclohexane (128184-69-0,134680-61-8) → (1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)cyclohexyl methanesulfonate (139402-99-6)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; at 25 ℃; for 12h; under 760 Torr;

DOI:10.1016/0008-6215(91)89017-A

upstream raw materials:

(1S,2R,3R,4R,5R,6S)-1,2,3-tribenzyloxy-6-methanesulfonyloxy-4-<(1-methylethyl)diethylsilyl>oxy-5-<<(1-methylethyl)diethylsilyl>oxy>methylcyclohexane

(1S,2S,3R,4S,5R,6R)-2,3,4,5-tetrakis(benzyloxy)-6-[(benzyloxy)methyl]cyclohexyl methanesulfonate

(4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one

(1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene

Downstream raw materials:

cyclophellitol