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

Base Information

• Chemical Name: ethyl (3R,6S,7R,8S,8aS)-8-benzyloxy-6,7-dihydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate
• CAS No.: 540533-94-6
• Molecular Formula: C₁₇H₂₁NO₆S
• Molecular Weight: 367.423
• Mol file: 540533-94-6.mol

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

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

There total 2 articles about ethyl (3R,6S,7R,8S,8aS)-8-benzyloxy-6,7-dihydroxy-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: 34.0%

benzyl bromide (100-39-0) + ethyl (3R,6S,7R,8S,8aS)-8-hydroxy-6,7-isopropylidene-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate (540533-93-5) → ethyl (3R,6S,7R,8S,8aS)-8-benzyloxy-6,7-dihydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate (540533-94-6) + ethyl 2-[(2S,3S,4R,5S)-3-benzyloxy-2-benzylsulfanyl-4,5-dihydroxy-6-oxopiperidin-1-yl]acrylate

Guidance literature:

benzyl bromide; ethyl (3R,6S,7R,8S,8aS)-8-hydroxy-6,7-isopropylidene-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate; With sodium hydride; In N,N-dimethyl-formamide; for 1.5h;

With trifluoroacetic acid; In ethanol; at 20 ℃; for 15h; Further stages.;

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 → ethyl (3R,6S,7R,8S,8aS)-8-benzyloxy-6,7-dihydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate (540533-94-6)

Guidance literature:

Multi-step reaction with 2 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

With sulfuric acid; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200390133

Reference yield: 38.0%

trifluoromethylsulfonic anhydride (358-23-6) + ethyl (3R,6S,7R,8S,8aS)-8-benzyloxy-6,7-dihydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate (540533-94-6) → ethyl (3R,8S,8aS)-8-benzyloxy-5-oxo-6-(trifluoromethanesulfonyloxy)-2,3,8,8a-tetrahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate + 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 (540533-95-7)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/ejoc.200390133

upstream raw materials:

benzyl bromide

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

Downstream raw materials:

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

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