Acetic acid (1S,2R,5S,6R)-5,6-diacetoxy-2-chloro-2-hydroxymethyl-cyclohex-3-enyl ester

Base Information

• Chemical Name: Acetic acid (1S,2R,5S,6R)-5,6-diacetoxy-2-chloro-2-hydroxymethyl-cyclohex-3-enyl ester
• CAS No.: 81692-15-1
• Molecular Formula: C₁₃H₁₇ClO₇
• Molecular Weight: 320.727

Synonyms:Acetic acid (1S,2R,5S,6R)-5,6-diacetoxy-2-chloro-2-hydroxymethyl-cyclohex-3-enyl ester

Chemical Property of Acetic acid (1S,2R,5S,6R)-5,6-diacetoxy-2-chloro-2-hydroxymethyl-cyclohex-3-enyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Acetic acid (1S,2R,5S,6R)-5,6-diacetoxy-2-chloro-2-hydroxymethyl-cyclohex-3-enyl ester

There total 2 articles about Acetic acid (1S,2R,5S,6R)-5,6-diacetoxy-2-chloro-2-hydroxymethyl-cyclohex-3-enyl 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: 100.0%

DL-2,3,4-tri-O-acetyl-1,7-anhydro-(1,2,4/3)-1-C-hydroxymethyl-5-cyclohexene-1,2,3,4-tetrol (81692-14-0,81739-18-6,102490-45-9,102490-46-0) → Acetic acid (1S,2R,5S,6R)-5,6-diacetoxy-2-chloro-2-hydroxymethyl-cyclohex-3-enyl ester (81692-15-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 0 - 5 ℃; for 0.833333h;

DOI:10.1246/cl.1982.279

Reference yield:

DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol (74024-01-4) → Acetic acid (1S,2R,5S,6R)-5,6-diacetoxy-2-chloro-2-hydroxymethyl-cyclohex-3-enyl ester (81692-15-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 37 percent / 70percent m-chloroperoxybenzoic acid (mCPBA), NaHCO₃ / CH₂Cl₂ / 1 h / Ambient temperature

2: 100 percent / 12 M HCl / tetrahydrofuran / 1 h / 0 - 5 °C

With hydrogenchloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1246/bcsj.56.1161

Reference yield: 100.0%

acetic anhydride (108-24-7) + Acetic acid (1S,2R,5S,6R)-5,6-diacetoxy-2-chloro-2-hydroxymethyl-cyclohex-3-enyl ester (81692-15-1) → DL-tetra-O-acetyl-(1,3/2,4)-4-chloro-4-C-hydroxymethyl-5-cyclohexene-1,2,3-triol (81692-16-2,102490-47-1)

Guidance literature:

With sulfuric acid;

DOI:10.1246/cl.1982.279

upstream raw materials:

DL-2,3,4-tri-O-acetyl-1,7-anhydro-(1,2,4/3)-1-C-hydroxymethyl-5-cyclohexene-1,2,3,4-tetrol

DL-(1,3/2)-1,2,3-tri-O-acetyl-4-methylene-5-cyclohexene-1,2,3-triol

Downstream raw materials:

DL-tetra-O-acetyl-(1,3/2,4)-4-chloro-4-C-hydroxymethyl-5-cyclohexene-1,2,3-triol

Acetic acid (1R,4S,5S,6S)-4,5-diacetoxy-1-chloro-6-hydroxy-cyclohex-2-enylmethyl ester

DL-Tetra-O-acetyl-(1,3,6/2)-6-azido-4-(hydroxymethyl)-4-cyclohexene-1,2,3-triol

valienamine

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