ethyl (1S,3R,4R,5S)-5-[(benzyloxy)methyl]-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate

Base Information

• Chemical Name: ethyl (1S,3R,4R,5S)-5-[(benzyloxy)methyl]-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate
• CAS No.: 495397-73-4
• Molecular Formula: C₂₀H₂₄O₆
• Molecular Weight: 360.407
• Mol file: 495397-73-4.mol

Synonyms:ethyl (1S,3R,4R,5S)-5-[(benzyloxy)methyl]-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate

Chemical Property of ethyl (1S,3R,4R,5S)-5-[(benzyloxy)methyl]-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1S,3R,4R,5S)-5-[(benzyloxy)methyl]-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate

There total 4 articles about ethyl (1S,3R,4R,5S)-5-[(benzyloxy)methyl]-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate 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: 58.0%

ethyl (4R,5R)-2-diazo-6-[(benzyloxy)methyl]-4,5-isopropylenedioxy-3-oxo-6-heptenoate (495397-71-2) → ethyl (1S,3R,4R,5S)-5-[(benzyloxy)methyl]-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate (495397-73-4)

Guidance literature:

dirhodium tetraacetate; In toluene; for 2.5h; Heating;

DOI:10.1016/S0040-4020(02)01002-5

Reference yield: 27.0%

ethyl (4R,5R)-2-diazo-6-[(benzyloxy)methyl]-4,5-isopropylenedioxy-3-oxo-6-heptenoate (495397-71-2) → ethyl (1S,3R,4R,5S)-5-[(benzyloxy)methyl]-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate (495397-73-4) + ethyl (1R,3R,4R,5R)-5-[(benzyloxy)methyl]-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate

Guidance literature:

With copper(l) chloride; In toluene; for 2h; Heating;

DOI:10.1016/S0040-4020(02)01002-5

Reference yield:

ethyl (4R,5R)-6-[(benzyloxy)methyl]-4,5-isopropylenedioxy-3-oxo-6-heptenoate (495397-70-1) → ethyl (1S,3R,4R,5S)-5-[(benzyloxy)methyl]-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate (495397-73-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / tosyl azide; Et₃N / ethanol / 12 h / 20 °C

2: 58 percent / Rh₂(OAc)4 / toluene / 2.5 h / Heating

With 4-toluenesulfonyl azide; triethylamine; dirhodium tetraacetate; In ethanol; toluene;

DOI:10.1016/S0040-4020(02)01002-5

upstream raw materials:

ethyl (4R,5R)-2-diazo-6-[(benzyloxy)methyl]-4,5-isopropylenedioxy-3-oxo-6-heptenoate

(4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

ethyl (4R,5R)-6-[(benzyloxy)methyl]-4,5-isopropylenedioxy-3-oxo-6-heptenoate

Downstream raw materials:

ethyl (2R,3R,4R)-2-[(benzyloxy)methyl]-3,4-isopropylenedioxy-5-oxo-2-[(phenylthio)methyl]cyclopentanecarboxylate