(1R,2S,3S,4S,5S)-5-(acetoxymethyl)cyclohexane-1,2,3,4-tetrayl tetraacetate

Base Information

• Chemical Name: (1R,2S,3S,4S,5S)-5-(acetoxymethyl)cyclohexane-1,2,3,4-tetrayl tetraacetate
• CAS No.: 102629-12-9
• Molecular Formula: C₁₇H₂₄O₁₀
• Molecular Weight: 388.372

Synonyms:(1R,2S,3S,4S,5S)-5-(acetoxymethyl)cyclohexane-1,2,3,4-tetrayl tetraacetate

Chemical Property of (1R,2S,3S,4S,5S)-5-(acetoxymethyl)cyclohexane-1,2,3,4-tetrayl tetraacetate

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (1R,2S,3S,4S,5S)-5-(acetoxymethyl)cyclohexane-1,2,3,4-tetrayl tetraacetate

There total 96 articles about (1R,2S,3S,4S,5S)-5-(acetoxymethyl)cyclohexane-1,2,3,4-tetrayl tetraacetate 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: 98.0%

acetic anhydride (108-24-7) + (+/-)-2exo,3exo-diacetoxy-5endo-acxetoxymethyl-7-oxabicyclo<2.2.1>heptane (64589-25-9,90695-20-8,117772-63-1,117772-66-4) → DL-(1,2,3,4/5)-5-acethoxymethyl-1,2,3,4-tetra-O-acetyl-1,2,3,4-cyclohexanetetrol (10226-79-6,16656-57-8,16802-99-6,52079-86-4,60594-30-1,60594-31-2,64625-67-8,74560-70-6,74561-02-7,74561-06-1,74561-11-8,77209-45-1,90694-06-7,90695-22-0,94943-06-3,94943-07-4,97372-12-8,97372-20-8,97372-27-5,97372-29-7,102629-12-9,105017-73-0,105017-80-9,105368-83-0,108813-47-4,108813-49-6,108866-23-5,115184-61-7,115184-64-0)

Guidance literature:

With sulfuric acid; In acetic acid; at 90 ℃; for 45h;

DOI:10.1016/0008-6215(88)85054-7

Reference yield: 90.0%

acetic anhydride (108-24-7) + (1R,2R,3S,4R,5R)-5-Hydroxymethyl-cyclohexane-1,2,3,4-tetraol (10226-73-0,16656-62-5,16802-98-5,52079-85-3,64625-68-9,74560-71-7,74561-03-8,74561-07-2,74561-10-7,86117-80-8,86117-81-9,86117-82-0,90694-07-8,94943-08-5,94943-09-6,95043-48-4,96647-89-1,97372-13-9,97372-19-5,97372-28-6,97372-30-0,102629-13-0,105017-74-1,105017-81-0,108867-09-0,109668-67-9,135820-00-7) → DL-(1,2,3,5/4)-5-acethoxymethyl-1,2,3,4-tetra-O-acetyl-1,2,3,4-cyclohexanetetrol (10226-79-6,16656-57-8,16802-99-6,52079-86-4,60594-30-1,60594-31-2,64625-67-8,74560-70-6,74561-02-7,74561-06-1,74561-11-8,77209-45-1,90694-06-7,90695-22-0,94943-06-3,94943-07-4,97372-12-8,97372-20-8,97372-27-5,97372-29-7,102629-12-9,105017-73-0,105017-80-9,105368-83-0,108813-47-4,108813-49-6,108866-23-5,115184-61-7,115184-64-0)

Guidance literature:

With pyridine; In acetic acid; Ambient temperature;

DOI:10.1246/bcsj.53.1121

Reference yield: 66.0%

acetic anhydride (108-24-7) + (1RS,2SR,3SR,4SR,5RS)-2,3,4-triacetoxy-6-oxabicyclo<3.2.1>octane (108794-46-3) → DL-(1,3,4,5/2)-1,2,3,4-tetra-acetoxy-5-acetoxymethylcyclohexane (10226-79-6,16656-57-8,16802-99-6,52079-86-4,60594-30-1,60594-31-2,64625-67-8,74560-70-6,74561-02-7,74561-06-1,74561-11-8,77209-45-1,90694-06-7,90695-22-0,94943-06-3,94943-07-4,97372-12-8,97372-20-8,97372-27-5,97372-29-7,102629-12-9,105017-73-0,105017-80-9,105368-83-0,108813-47-4,108813-49-6,108866-23-5,115184-61-7,115184-64-0)

Guidance literature:

With sulfuric acid; acetic acid; at 50 ℃; for 48h;

DOI:10.1016/S0008-6215(00)90192-7

upstream raw materials:

acetic anhydride

(1S,2S,3S,4S,5R)-2-acetoxy-1-acetoxymethyl-3,4,5-tris(benzyloxy)cyclohexane

(1R,3R,4S,5S,6S,8R,9R)-3,4,5-trihydroxy-8,9-isopropylidenedioxy-7-oxabicyclo<4.3.0>nonane

(3R,3aS,5R,6S,7S,7aS)-5,6,7-Tris-benzyloxy-octahydro-benzofuran-2,3-diol

Downstream raw materials:

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

Pseudo-α-DL-talopyranose; 2c,3c,4c,5t-Tetrahydroxy-1-cyclohexan-methanol

Pseudo-β-DL-gulopyranose; DL-1-Hydroxymethyl-2,3,4,5-tetrahydroxy-cyclohexan

(1SR,3SR,5SR,8RS,10SR,12RS)-5,12-diphenyl-4,6,11,13-tetraoxatricyclo<8.3.0.0^3,8>tridecan-2-one

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