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

Base Information

• Chemical Name: (1S,2S,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-en-2-ol
• CAS No.: 94903-43-2
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.289
• Mol file: 94903-43-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (1S,2S,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-en-2-ol 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: 72.0%

methyl 4-epi-shikimate (4372-89-8,4372-91-2,14671-74-0,16613-43-7,16613-44-8,40983-58-2,121468-33-5,141781-68-2) + benzaldehyde (100-52-7) → methyl (1α,5α,6α)-5-hydroxy-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene-3-carboxylate (80631-78-3,80631-88-5,94903-41-0,94903-43-2,116183-40-5)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; Heating;

DOI:10.1021/ja00389a025

Reference yield:

(1S,6R)-5-Hydroxy-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester (78844-86-7,78961-89-4,83648-86-6,90866-42-5,90866-43-6) → methyl (1α,5α,6α)-5-hydroxy-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene-3-carboxylate (80631-78-3,80631-88-5,94903-41-0,94903-43-2,116183-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) NaOCH₃ / 1.) reflux, 1.25 h, 2.) MeOH, room temperature, 1.5 h

2: 72 percent / p-toluenesulfonic acid / toluene / Heating

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

DOI:10.1021/ja00389a025

Reference yield:

(3aR,7aR)-7-Oxo-2-phenyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester → (1S,2S,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-en-2-ol (94903-43-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; Yield given;

DOI:10.1021/jo00206a035

upstream raw materials:

benzaldehyde

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

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

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

Downstream raw materials:

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

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

2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl ester

methyl (1α,5α,6α)-5--8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene-3-carboxylate