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

Base Information

• Chemical Name: ethyl (4R,5R)-2-diazo-6-[(benzyloxy)methyl]-4,5-isopropylenedioxy-3-oxo-6-heptenoate
• CAS No.: 495397-71-2
• Molecular Formula: C₂₀H₂₄N₂O₆
• Molecular Weight: 388.42
• Mol file: 495397-71-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about ethyl (4R,5R)-2-diazo-6-[(benzyloxy)methyl]-4,5-isopropylenedioxy-3-oxo-6-heptenoate 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: 90.0%

ethyl (4R,5R)-6-[(benzyloxy)methyl]-4,5-isopropylenedioxy-3-oxo-6-heptenoate (495397-70-1) → ethyl (4R,5R)-2-diazo-6-[(benzyloxy)methyl]-4,5-isopropylenedioxy-3-oxo-6-heptenoate (495397-71-2)

Guidance literature:

With 4-toluenesulfonyl azide; triethylamine; In ethanol; at 20 ℃; for 12h;

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

Reference yield:

(4R,5R)-5-(1-Benzyloxymethyl-vinyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (495397-67-6) → ethyl (4R,5R)-2-diazo-6-[(benzyloxy)methyl]-4,5-isopropylenedioxy-3-oxo-6-heptenoate (495397-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / SnCl₂ / CH₂Cl₂ / 2 h / 0 °C

2: 90 percent / tosyl azide; Et₃N / ethanol / 12 h / 20 °C

With 4-toluenesulfonyl azide; triethylamine; tin(ll) chloride; In ethanol; dichloromethane;

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

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

upstream raw materials:

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

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

Downstream raw materials:

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

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