(1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol

Base Information

• Chemical Name: (1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol
• CAS No.: 94843-95-5
• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.304
• Mol file: 94843-95-5.mol

Synonyms:(1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol

Chemical Property of (1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol

There total 3 articles about (1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol 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: 97.0%

methanol (67-56-1) + (1S,3R,5RS,7R,8R)-5-phenyl-10-oxo-4,6,9-trioxatricyclo<6.2.11,8.03,7>undecan-1-ol (32384-44-4,92282-37-6,94903-42-1) → (1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol (94843-95-5)

Guidance literature:

With sodium methylate; for 1h; Ambient temperature;

DOI:10.1021/jo00206a035

Reference yield:

benzaldehyde (100-52-7) → (1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol (94843-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid monohydrate / benzene / 12 h / Heating

2: 97 percent / NaOMe / 1 h / Ambient temperature

With sodium methylate; toluene-4-sulfonic acid; In benzene;

DOI:10.1021/jo00206a035

Reference yield:

(1R,3R,4S)-1,3,4,5-Tetrahydroxy-cyclohexanecarboxylic acid (77-95-2) → (1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol (94843-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid monohydrate / benzene / 12 h / Heating

2: 97 percent / NaOMe / 1 h / Ambient temperature

With sodium methylate; toluene-4-sulfonic acid; In benzene;

DOI:10.1021/jo00206a035

upstream raw materials:

methanol

(1S,3R,5RS,7R,8R)-5-phenyl-10-oxo-4,6,9-trioxatricyclo<6.2.1^1,8.0^3,7>undecan-1-ol

benzaldehyde

(1R,3R,4S)-1,3,4,5-Tetrahydroxy-cyclohexanecarboxylic acid

Downstream raw materials:

(-)-methyl 4,5-O-benzylidene-4-epi-shikimate

(1S,2S,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-en-2-ol

(1R,2R,6R,8S)-2-(benzoyloxy)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene

(3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid