((1S,4S,5R,6R)-4,5,6-Triacetoxy-cyclohex-2-enyl)-acetic acid

Base Information

• Chemical Name: ((1S,4S,5R,6R)-4,5,6-Triacetoxy-cyclohex-2-enyl)-acetic acid
• CAS No.: 135346-52-0
• Molecular Formula: C₁₄H₁₈O₈
• Molecular Weight: 314.292
• Mol file: 135346-52-0.mol

Synonyms:((1S,4S,5R,6R)-4,5,6-Triacetoxy-cyclohex-2-enyl)-acetic acid

Chemical Property of ((1S,4S,5R,6R)-4,5,6-Triacetoxy-cyclohex-2-enyl)-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1S,4S,5R,6R)-4,5,6-Triacetoxy-cyclohex-2-enyl)-acetic acid

There total 4 articles about ((1S,4S,5R,6R)-4,5,6-Triacetoxy-cyclohex-2-enyl)-acetic acid 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: 82.0%

Acetic acid (1S,2S,5R,6S)-5,6-diacetoxy-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-cyclohex-3-enyl ester (135346-51-9) → ((1S,4S,5R,6R)-4,5,6-Triacetoxy-cyclohex-2-enyl)-acetic acid (135346-52-0)

Guidance literature:

With water; acetic acid; at 70 ℃;

DOI:10.1016/S0040-4039(00)74357-7

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) → ((1S,4S,5R,6R)-4,5,6-Triacetoxy-cyclohex-2-enyl)-acetic acid (135346-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / (Ph₃P)Pd / dimethylformamide / 70 °C

2: 82 percent / AcOH, water / 70 °C

With water; acetic acid; (PH₃P)Pd; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)74357-7

Reference yield:

1(3),4(6),5,6(4)-tetra-O-acetyl-sn-myo-inositol (13462-79-8,80953-32-8,90366-30-6,108032-48-0,113973-54-9,113973-61-8) → ((1S,4S,5R,6R)-4,5,6-Triacetoxy-cyclohex-2-enyl)-acetic acid (135346-52-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / DMAP

2: 89 percent / (MeO)3P / 110 °C

3: 73 percent / (Ph₃P)Pd / dimethylformamide / 70 °C

4: 82 percent / AcOH, water / 70 °C

With dmap; water; acetic acid; phosphorous acid trimethyl ester; (PH₃P)Pd; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)74357-7

upstream raw materials:

Acetic acid (1S,2S,5R,6S)-5,6-diacetoxy-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-cyclohex-3-enyl ester

1⁽³⁾,4⁽⁶⁾,5,6⁽⁴⁾-tetra-O-acetyl-sn-myo-inositol

(+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol

Acetic acid (3aR,4R,5S,6S,7R,7aS)-5,6,7-triacetoxy-2-thioxo-hexahydro-benzo[1,3]dioxol-4-yl ester

Downstream raw materials:

((1S,4S,5R,6R)-4,5,6-Triacetoxy-cyclohex-2-enyl)-acetic acid 2-thioxo-2H-pyridin-1-yl ester

(1SR,2RS,3SR,6RS)-1,2,3-triacetoxy-6-(acetoxymethyl)cyclohex-4-ene