(Z)-(3R,9R)-3-Benzyloxycarbonylamino-9-methyl-2-oxo-3,4,8,9-tetrahydro-2H-[1,5]oxathionine-6-carboxylic acid methyl ester

Base Information

Chemical Name:(Z)-(3R,9R)-3-Benzyloxycarbonylamino-9-methyl-2-oxo-3,4,8,9-tetrahydro-2H-[1,5]oxathionine-6-carboxylic acid methyl ester
CAS No.:105815-30-3
Molecular Formula:C₁₈H₂₁NO₆S
Molecular Weight:379.434
Hs Code.:

Synonyms:(Z)-(3R,9R)-3-Benzyloxycarbonylamino-9-methyl-2-oxo-3,4,8,9-tetrahydro-2H-[1,5]oxathionine-6-carboxylic acid methyl ester

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Chemical Property of (Z)-(3R,9R)-3-Benzyloxycarbonylamino-9-methyl-2-oxo-3,4,8,9-tetrahydro-2H-[1,5]oxathionine-6-carboxylic acid methyl ester

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Technology Process of (Z)-(3R,9R)-3-Benzyloxycarbonylamino-9-methyl-2-oxo-3,4,8,9-tetrahydro-2H-[1,5]oxathionine-6-carboxylic acid methyl ester

There total 9 articles about (Z)-(3R,9R)-3-Benzyloxycarbonylamino-9-methyl-2-oxo-3,4,8,9-tetrahydro-2H-[1,5]oxathionine-6-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: 39.0%

: 98051-43-5
(Z)-(S)-2-((R)-2-Benzyloxycarbonylamino-2-carboxy-ethylsulfanyl)-5-hydroxy-hex-2-enoic acid methyl ester

: 105815-30-3
(Z)-(3R,9R)-3-Benzyloxycarbonylamino-9-methyl-2-oxo-3,4,8,9-tetrahydro-2H-[1,5]oxathionine-6-carboxylic acid methyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In benzene; for 48h; Ambient temperature;
DOI:10.1021/jo00376a052

Reference yield:

: 105729-35-9
methyl 3-oxo-5(S)-<(tert-butyldimethylsilyl)oxy>hexanoate

: 105815-30-3
(Z)-(3R,9R)-3-Benzyloxycarbonylamino-9-methyl-2-oxo-3,4,8,9-tetrahydro-2H-[1,5]oxathionine-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 15 min

2: 58 percent / sodium borohydride / methanol / 0.25 h

3: 73 percent / triethylamine, methanesulfonyl chloride / CH₂Cl₂ / 0.42 h / Ambient temperature

4: 84 percent / acetic acid / H₂O / 23 h / Ambient temperature

5: 93 percent / trifluoroacetic acid / 0.92 h

6: 39 percent / PPh₃, diethyl azodicarboxylate / benzene / 48 h / Ambient temperature

With sodium tetrahydroborate; sodium hydride; acetic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In methanol; dichloromethane; water; benzene;
DOI:10.1021/jo00376a052

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 105815-30-3
(Z)-(3R,9R)-3-Benzyloxycarbonylamino-9-methyl-2-oxo-3,4,8,9-tetrahydro-2H-[1,5]oxathionine-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 76 percent / aq. KHCO₃ / CHCl₃ / 0.5 h

2: 1.) sulfur chloride / 1.) 1,2-dichloroethane, 0 deg C, 5 min, 2.) 1,2-dichloroethane, a) 0 deg C, 10 min, b) RT, 90 min

3: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 15 min

4: 58 percent / sodium borohydride / methanol / 0.25 h

5: 73 percent / triethylamine, methanesulfonyl chloride / CH₂Cl₂ / 0.42 h / Ambient temperature

6: 84 percent / acetic acid / H₂O / 23 h / Ambient temperature

7: 93 percent / trifluoroacetic acid / 0.92 h

8: 39 percent / PPh₃, diethyl azodicarboxylate / benzene / 48 h / Ambient temperature

With sodium tetrahydroborate; sulfur dichloride; sodium hydride; potassium hydrogencarbonate; acetic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In methanol; dichloromethane; chloroform; water; benzene;
DOI:10.1021/jo00376a052