(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
Hs Code.:
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;

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

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
(1S,5S,6R)-5-(Acetyloxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylicAcidMethylEster
50mg
$ 195.00

Medical Isotopes, Inc.
(1S,5S,6R)-5-(Acetyloxy)-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylicAcidMethylEster
500 mg
$ 2400.00

Total 2 raw suppliers

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:

99% ^*data from raw suppliers

(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%

: 108-05-4,9003-20-7
vinyl acetate

: 78844-86-7,78961-89-4,83648-86-6,90866-42-5,90866-43-6
rac-(1R,5R,6S)-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-en-5-ol

: 78844-86-7
methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate

: 494195-98-1
(1S,5S,6R)-5-acetoxy-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-ene

Guidance literature:: With Pseudomonas stutzeri lipase; at 20 ℃; for 40h;
DOI:10.1016/S0040-4039(02)02271-2

Reference yield:

: 89678-08-0,95977-83-6,141318-30-1
rac-(1R,2R,3R,6R,7S)-2-iodo-4,8-dioxatricyclo[4.2.1.0^3,7]nonan-5-one

: 494195-98-1
(1S,5S,6R)-5-acetoxy-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-ene

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:

: 84752-05-6,58564-81-1,58564-80-0
7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic chloride

: 494195-98-1
(1S,5S,6R)-5-acetoxy-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-ene

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