(1S,5S,6R)-5-(Acetyloxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylic Acid Methyl Ester

Base Information

• Chemical Name: (1S,5S,6R)-5-(Acetyloxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylic Acid Methyl Ester
• CAS No.: 494195-98-1
• Molecular Formula: C10H12O5
• Molecular Weight: 212.19900
• Mol file: 494195-98-1.mol

Synonyms:(1S,5S,6R)-5-(Acetyloxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylic Acid Methyl Ester;

Chemical Property of (1S,5S,6R)-5-(Acetyloxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylic Acid Methyl Ester

Chemical Property:

• Boiling Point: 291.6±40.0 °C(Predicted)
• PSA: 65.13000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 0.18860

Purity/Quality:

(1S,5S,6R)-5-(Acetyloxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (1S,5S,6R)-5-(Acetyloxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylic Acid Methyl Ester is an intermediate for the synthesis of epoxyquinols A, B, and C.

Technology Process of (1S,5S,6R)-5-(Acetyloxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylic Acid Methyl Ester

There total 4 articles about (1S,5S,6R)-5-(Acetyloxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylic Acid Methyl 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: 49.0%

vinyl acetate (108-05-4,9003-20-7) + rac-(1R,5R,6S)-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-en-5-ol (78844-86-7,78961-89-4,83648-86-6,90866-42-5,90866-43-6) → methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate (78844-86-7) + (1S,5S,6R)-5-acetoxy-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-ene (494195-98-1)

Guidance literature:

With Pseudomonas stutzeri lipase; at 20 ℃; for 40h;

DOI:10.1016/S0040-4039(02)02271-2

Reference yield:

rac-(1R,2R,3R,6R,7S)-2-iodo-4,8-dioxatricyclo[4.2.1.03,7]nonan-5-one (89678-08-0,95977-83-6,141318-30-1) → (1S,5S,6R)-5-acetoxy-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-ene (494195-98-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: KOH / dimethylformamide / 17 h / 60 °C

1.2: 90 percent / dimethylformamide / 2 h / 20 °C / sonication

2.1: 92 percent / diisopropylamine; nBuLi / tetrahydrofuran; hexane / 0.17 h / -90 °C

3.1: 48 percent / Pseudomonas stutzeri lipase (Meito TL) / 40 h / 20 °C

With potassium hydroxide; n-butyllithium; Pseudomonas stutzeri lipase (Meito TL); diisopropylamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jo048425h

Reference yield:

7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic chloride (84752-05-6,58564-81-1,58564-80-0) → (1S,5S,6R)-5-acetoxy-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-ene (494195-98-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaOH; NaHCO₃ / H₂O / 1.5 h

1.2: I₂ / H₂O; CH₂Cl₂ / 2 h / 0 °C

2.1: KOH / dimethylformamide / 17 h / 60 °C

2.2: 90 percent / dimethylformamide / 2 h / 20 °C / sonication

3.1: 92 percent / diisopropylamine; nBuLi / tetrahydrofuran; hexane / 0.17 h / -90 °C

4.1: 48 percent / Pseudomonas stutzeri lipase (Meito TL) / 40 h / 20 °C

With potassium hydroxide; sodium hydroxide; n-butyllithium; Pseudomonas stutzeri lipase (Meito TL); sodium hydrogencarbonate; diisopropylamine; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo048425h

upstream raw materials:

vinyl acetate

rac-(1R,5R,6S)-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-en-5-ol

rac-(1R,2R,3R,6R,7S)-2-iodo-4,8-dioxatricyclo[4.2.1.0^3,7]nonan-5-one

7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic chloride