(3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one

Base Information

• Chemical Name: (3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one
• CAS No.: 35761-79-6
• Molecular Formula: C₁₅H₁₆O₃
• Molecular Weight: 244.29
• Mol file: 35761-79-6.mol

Synonyms:(3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one

Chemical Property of (3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one

There total 10 articles about (3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one 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: 100.0%

(1S,5R,6S,7R)-6-benzyloxymethyl-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one (38931-62-3) → (3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one (35761-79-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 1h; Ambient temperature;

Reference yield: 87.0%

(3aR,4S,6R,6aR)-4-Benzyloxymethyl-6-iodohexahydrocyclopenta[b]furan-2-one (193071-28-2) → (3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one (35761-79-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 3h; Heating;

DOI:10.1055/s-1997-3253

Reference yield: 35.0%

(1R,4S,7R)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-one → (3aS,4R,6aR)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one (51262-71-6) + (3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one (35761-79-6) + (1R,2R,4S,7R)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ol (53121-27-0) + (1S,2R,4R,7S)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ol (133520-33-9)

Guidance literature:

With Tetraethyl pyrophosphate; Further byproducts given. Yields of byproduct given; Acinetobacter calcoaceticus NCIB 9871 (grown on 1,2-cyclohexanediol);

DOI:10.1016/S0040-4039(00)79478-0

upstream raw materials:

(1S,5R,6S,7R)-6-benzyloxymethyl-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one

(1R,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-2-one

(3aR,4S,6R,6aR)-4-Benzyloxymethyl-6-iodohexahydrocyclopenta[b]furan-2-one

(1R,4S)-4-(hydroxymethyl)cyclopent-2-enol

Downstream raw materials:

(1S,2R,3S)-3-Benzyloxymethyl-2-(2-phenylselanyl-ethyl)-cyclopentanol