(3S,4aS,5S,7S,8aR)-7-Acetoxy-5-(2-acetoxy-ethyl)-3-benzyl-4a-cyano-2-oxo-octahydro-benzo[1,4]oxazine-7-carboxylic acid methyl ester

Base Information

Chemical Name:(3S,4aS,5S,7S,8aR)-7-Acetoxy-5-(2-acetoxy-ethyl)-3-benzyl-4a-cyano-2-oxo-octahydro-benzo[1,4]oxazine-7-carboxylic acid methyl ester
CAS No.:1054771-90-2
Molecular Formula:C₂₄H₂₈N₂O₈
Molecular Weight:472.495
Hs Code.:

Synonyms:(3S,4aS,5S,7S,8aR)-7-Acetoxy-5-(2-acetoxy-ethyl)-3-benzyl-4a-cyano-2-oxo-octahydro-benzo[1,4]oxazine-7-carboxylic acid methyl ester

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Chemical Property of (3S,4aS,5S,7S,8aR)-7-Acetoxy-5-(2-acetoxy-ethyl)-3-benzyl-4a-cyano-2-oxo-octahydro-benzo[1,4]oxazine-7-carboxylic acid methyl ester

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Technology Process of (3S,4aS,5S,7S,8aR)-7-Acetoxy-5-(2-acetoxy-ethyl)-3-benzyl-4a-cyano-2-oxo-octahydro-benzo[1,4]oxazine-7-carboxylic acid methyl ester

There total 8 articles about (3S,4aS,5S,7S,8aR)-7-Acetoxy-5-(2-acetoxy-ethyl)-3-benzyl-4a-cyano-2-oxo-octahydro-benzo[1,4]oxazine-7-carboxylic 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:

: 915090-85-6
(1S,3S,5R)-1-Acetoxy-3-(2-acetoxy-ethyl)-5-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxy)-4-oxo-cyclohexanecarboxylic acid methyl ester

: 7677-24-9
trimethylsilyl cyanide

: 1054771-90-2
(3S,4aS,5S,7S,8aR)-7-Acetoxy-5-(2-acetoxy-ethyl)-3-benzyl-4a-cyano-2-oxo-octahydro-benzo[1,4]oxazine-7-carboxylic acid methyl ester

Guidance literature:: (1S,3S,5R)-1-Acetoxy-3-(2-acetoxy-ethyl)-5-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionyloxy)-4-oxo-cyclohexanecarboxylic acid methyl ester; With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1h;

trimethylsilyl cyanide; With water; zinc(II) chloride; In isopropyl alcohol; at 20 ℃; for 2.5h;
DOI:10.1021/ol062098d

Reference yield:

: 915090-87-8
(1S,3S,4R,5R)-1-Acetoxy-3-(2-acetoxy-ethyl)-4,5-dihydroxy-cyclohexanecarboxylic acid methyl ester

: 1054771-90-2
(3S,4aS,5S,7S,8aR)-7-Acetoxy-5-(2-acetoxy-ethyl)-3-benzyl-4a-cyano-2-oxo-octahydro-benzo[1,4]oxazine-7-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / DMAP; EDCl / CH₂Cl₂ / 21 h / 20 °C

2.1: 86 percent / PDC / CH₂Cl₂ / 24 h / 20 °C

3.1: 2,6-lutidine; TMSOTf / CH₂Cl₂ / 1 h / 20 °C

3.2: ZnCl₂; H₂O / propan-2-ol / 2.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; dipyridinium dichromate; trimethylsilyl trifluoromethanesulfonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;
DOI:10.1021/ol062098d

Reference yield:

: 915090-86-7
(2S,3S,4aR,6S,8S,8aR)-8-Allyl-6-hydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

: 1054771-90-2
(3S,4aS,5S,7S,8aR)-7-Acetoxy-5-(2-acetoxy-ethyl)-3-benzyl-4a-cyano-2-oxo-octahydro-benzo[1,4]oxazine-7-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: ozone / methanol / 0.25 h / -78 °C

1.2: 70 percent / NaBH₄ / methanol / 0.5 h / 0 °C

2.1: 97 percent / DMAP / CH₂Cl₂ / 6 h / 0 °C

3.1: 92 percent / TFA; H₂O / 0.17 h / 20 °C

4.1: 95 percent / DMAP; EDCl / CH₂Cl₂ / 21 h / 20 °C

5.1: 86 percent / PDC / CH₂Cl₂ / 24 h / 20 °C

6.1: 2,6-lutidine; TMSOTf / CH₂Cl₂ / 1 h / 20 °C

6.2: ZnCl₂; H₂O / propan-2-ol / 2.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; dipyridinium dichromate; trimethylsilyl trifluoromethanesulfonate; water; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1021/ol062098d