ethyl (3R,6R,7R,8S,8aS)-6-azido-8-benzyloxy-7-hydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate

Base Information

Chemical Name:ethyl (3R,6R,7R,8S,8aS)-6-azido-8-benzyloxy-7-hydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate
CAS No.:540533-96-8
Molecular Formula:C₁₇H₂₀N₄O₅S
Molecular Weight:392.436
Hs Code.:

Synonyms:ethyl (3R,6R,7R,8S,8aS)-6-azido-8-benzyloxy-7-hydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate

Suppliers and Price of ethyl (3R,6R,7R,8S,8aS)-6-azido-8-benzyloxy-7-hydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate

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

Total 0 raw suppliers

Chemical Property of ethyl (3R,6R,7R,8S,8aS)-6-azido-8-benzyloxy-7-hydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of ethyl (3R,6R,7R,8S,8aS)-6-azido-8-benzyloxy-7-hydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate

There total 5 articles about ethyl (3R,6R,7R,8S,8aS)-6-azido-8-benzyloxy-7-hydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-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: 83.0%

: 540533-95-7
ethyl (3R,6S,7R,8S,8aS)-8-benzyloxy-7-hydroxy-5-oxo-6-(trifluoromethanesulfonyloxy)hexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate

: 540533-96-8
ethyl (3R,6R,7R,8S,8aS)-6-azido-8-benzyloxy-7-hydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate

Guidance literature:: With sodium azide; 15-crown-5; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1002/ejoc.200390133

Reference yield:

: 100-39-0
benzyl bromide

: 540533-96-8
ethyl (3R,6R,7R,8S,8aS)-6-azido-8-benzyloxy-7-hydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 1.5 h

1.2: 34 percent / TFA / aq. ethanol / 15 h / 20 °C

2.1: 38 percent / DMAP; pyridine / CH₂Cl₂ / 2 h / 20 °C

3.1: 83 percent / NaN₃; 15-crown-5 / CH₂Cl₂ / 16 h / 20 °C

With pyridine; dmap; sodium azide; 15-crown-5; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200390133

Reference yield:

: (3R,6S,7R,8S,8aS)-6,7,8-Trihydroxy-5-oxo-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ethyl ester

: 540533-96-8
ethyl (3R,6R,7R,8S,8aS)-6-azido-8-benzyloxy-7-hydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / cc. sulfuric acid / 1 h / 0 - 20 °C

2.1: NaH / dimethylformamide / 1.5 h

2.2: 34 percent / TFA / aq. ethanol / 15 h / 20 °C

3.1: 38 percent / DMAP; pyridine / CH₂Cl₂ / 2 h / 20 °C

4.1: 83 percent / NaN₃; 15-crown-5 / CH₂Cl₂ / 16 h / 20 °C

With pyridine; dmap; sodium azide; 15-crown-5; sulfuric acid; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200390133