[(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-(imidazole-1-carbothioyloxy)-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester

Base Information

• Chemical Name: [(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-(imidazole-1-carbothioyloxy)-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester
• CAS No.: 708197-73-3
• Molecular Formula: C₃₃H₃₉N₃O₆SSe
• Molecular Weight: 684.715

Synonyms:[(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-(imidazole-1-carbothioyloxy)-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester

Chemical Property of [(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-(imidazole-1-carbothioyloxy)-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester

Chemical Property:

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Technology Process of [(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-(imidazole-1-carbothioyloxy)-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester

There total 3 articles about [(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-(imidazole-1-carbothioyloxy)-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester 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: 91.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + [(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-hydroxy-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester (264218-58-8) → [(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-(imidazole-1-carbothioyloxy)-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester (708197-73-3)

Guidance literature:

With dmap; In toluene; for 3h; Heating;

DOI:10.1021/jo049724+

Reference yield:

(1R,1'S,8aR)-1-((1'-phenylmethoxy)hexane)-1,2,8,8a-tetrahydro-8-phenylselenyl-2-oxaindolizine-3,7-dione → [(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-(imidazole-1-carbothioyloxy)-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester (708197-73-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / -78 °C

2: 65 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h

3: 91 percent / 4-dimethylaminopyridine / toluene / 3 h / Heating

With dmap; sodium tetrahydroborate; cerium(III) chloride; boron trifluoride diethyl etherate; In methanol; dichloromethane; toluene; 1: Mukaiyama-Michael reaction / 2: Luche reduction;

DOI:10.1021/jo049724+

Reference yield:

[(1R,5R,8aS)-1-((S)-1-Benzyloxy-hexyl)-3,7-dioxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester → [(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-(imidazole-1-carbothioyloxy)-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester (708197-73-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h

2: 91 percent / 4-dimethylaminopyridine / toluene / 3 h / Heating

With dmap; sodium tetrahydroborate; cerium(III) chloride; In methanol; toluene; 1: Luche reduction;

DOI:10.1021/jo049724+

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

[(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-hydroxy-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester

Downstream raw materials:

(1R,1'S,5R,8aR)-3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl acetic acid methyl ester

[(1R,1'S,5R,9R)-3-oxo-1-((1'-phenylmethoxy)hexyl)-1,5,6,8a-tetrahydrooxazolo[3,4-a]pyridin-5-yl]acetic acid chloride

(1'R,2R,2'S,6R)-N-benzyl-2-[6-(2'-phenylmethoxy-1'-hydroxy-heptyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-N-(4-hydroxy-butyl)-acetamide

(1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide

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