(4aS,6S,8aS)-6-Methylsulfanylthiocarboxyoxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid ethyl ester

Base Information

Chemical Name:(4aS,6S,8aS)-6-Methylsulfanylthiocarboxyoxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid ethyl ester
CAS No.:97523-18-7
Molecular Formula:C₂₀H₂₇NO₃S₂
Molecular Weight:393.571
Hs Code.:

Synonyms:(4aS,6S,8aS)-6-Methylsulfanylthiocarboxyoxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid ethyl ester

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Chemical Property of (4aS,6S,8aS)-6-Methylsulfanylthiocarboxyoxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid ethyl ester

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Technology Process of (4aS,6S,8aS)-6-Methylsulfanylthiocarboxyoxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid ethyl ester

There total 13 articles about (4aS,6S,8aS)-6-Methylsulfanylthiocarboxyoxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid ethyl 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:

: (4aS,6S,8aS)-6-Dithiocarboxyoxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid ethyl ester

: 74-88-4
methyl iodide

: 97523-18-7
(4aS,6S,8aS)-6-Methylsulfanylthiocarboxyoxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid ethyl ester

Guidance literature:: With 1H-imidazole; In carbon disulfide; at 65 ℃; for 0.666667h; Yield given;
DOI:10.1021/jo00219a006

Reference yield:

: 17605-06-0
ethyl 3-oxohept-6-enoate

: 97523-18-7
(4aS,6S,8aS)-6-Methylsulfanylthiocarboxyoxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: NaBH₄ / propan-2-ol / 0.5 h / 0 °C

2: pyridine / 2 h / 80 °C

3: 72 percent / 1,7-diazabicyclo<5.4.0>undec-7-ene (DBU) / benzene / 2 h / Heating

4: 94 percent / CuI / diethyl ether / 1.5 h / 0 °C

5: 75 percent / NaOH / ethanol / 2 h / Heating

6: Et₃N, ClCOOMe, NaN₃ / acetone / 1.5 h / Ambient temperature

7: toluene / 3 h / Heating

8: 88 percent / sodium formate / 3 h / Ambient temperature

9: 95 percent / formic acid / 1.5 h / Ambient temperature

10: 95 percent / 3N aq. NaOH / ethanol / 0.5 h / Ambient temperature

11: 1.) NaH, imidazole / 1.) 65 deg C, 10 min, 2.) 65 deg C

12: imidazole / CS₂ / 0.67 h / 65 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; formic acid; sodium azide; sodium formate; sodium hydride; triethylamine; methyl chloroformate; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In carbon disulfide; diethyl ether; ethanol; isopropyl alcohol; acetone; toluene; benzene;
DOI:10.1021/jo00219a006

Reference yield:

: 87046-26-2
((Z)-3-Phenyl-octa-3,7-dienyl)-carbamic acid ethyl ester

: 97523-18-7
(4aS,6S,8aS)-6-Methylsulfanylthiocarboxyoxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / sodium formate / 3 h / Ambient temperature

2: 95 percent / formic acid / 1.5 h / Ambient temperature

3: 95 percent / 3N aq. NaOH / ethanol / 0.5 h / Ambient temperature

4: 1.) NaH, imidazole / 1.) 65 deg C, 10 min, 2.) 65 deg C

5: imidazole / CS₂ / 0.67 h / 65 °C

With 1H-imidazole; sodium hydroxide; formic acid; sodium formate; sodium hydride; In carbon disulfide; ethanol;
DOI:10.1021/jo00219a006