(1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbothioic acid S-ethyl ester

Base Information

• Chemical Name: (1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbothioic acid S-ethyl ester
• CAS No.: 177977-13-8
• Molecular Formula: C₂₅H₃₄O₄S
• Molecular Weight: 430.609
• Mol file: 177977-13-8.mol

Synonyms:(1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbothioic acid S-ethyl ester

Chemical Property of (1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbothioic acid S-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbothioic acid S-ethyl ester

There total 3 articles about (1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbothioic acid S-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: 91.1%

(4R,5S)-3-{(1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbonyl}-4-methyl-5-phenyl-oxazolidin-2-one (177977-03-6) + ethanethiol (75-08-1) → (1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbothioic acid S-ethyl ester (177977-13-8)

Guidance literature:

ethanethiol; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

(4R,5S)-3-{(1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbonyl}-4-methyl-5-phenyl-oxazolidin-2-one; In tetrahydrofuran; hexane; at 0 ℃; for 1.5h; Further stages.;

DOI:10.1002/1521-3765(20011001)7:19<4107::AID-CHEM4107>3.0.CO;2-K

Reference yield:

(4R,5S)-3-((E)-5-{2-[(2E,4E)-9-(4-Methoxy-benzyloxy)-nona-2,4-dienyl]-[1,3]dithian-2-yl}-pent-2-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one (177976-99-7) → (1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbothioic acid S-ethyl ester (177977-13-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 85.1 percent / Me₂AlCl / hexane; CH₂Cl₂ / -20 °C / 72 Torr

2.1: 80 percent / N-chlorosuccinimide; aq. AgNO₃ / acetonitrile / 0.33 h / 0 °C

3.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

3.2: 91.1 percent / hexane; tetrahydrofuran / 1.5 h / 0 °C

With N-chloro-succinimide; n-butyllithium; dimethylaluminum chloride; silver nitrate; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 1.1: intramolecular asymmetric Diels-Alder reaction;

DOI:10.1002/1521-3765(20011001)7:19<4107::AID-CHEM4107>3.0.CO;2-K

Reference yield:

C36H45NO5S2 (177977-02-5) → (1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbothioic acid S-ethyl ester (177977-13-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 80 percent / N-chlorosuccinimide; aq. AgNO₃ / acetonitrile / 0.33 h / 0 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

2.2: 91.1 percent / hexane; tetrahydrofuran / 1.5 h / 0 °C

With N-chloro-succinimide; n-butyllithium; silver nitrate; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1002/1521-3765(20011001)7:19<4107::AID-CHEM4107>3.0.CO;2-K

upstream raw materials:

(4R,5S)-3-{(1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbonyl}-4-methyl-5-phenyl-oxazolidin-2-one

ethanethiol

(4R,5S)-3-((E)-5-{2-[(2E,4E)-9-(4-Methoxy-benzyloxy)-nona-2,4-dienyl]-[1,3]dithian-2-yl}-pent-2-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

C₃₆H₄₅NO₅S₂

Downstream raw materials:

{(1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-7-trimethylsilanyloxy-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl}-carbamic acid methyl ester

(3aR,4S,7R,7aR)-4-Carboxymethyl-2-hydroxy-7-[4-(4-methoxy-benzyloxy)-butyl]-2,3,3a,4,7,7a-hexahydro-indole-1-carboxylic acid methyl ester

(1S,3aS,4R,5R,5aR,8aR,8bS)-4-Allyl-7-methoxy-5-[4-(4-methoxy-benzyloxy)-butyl]-1-methyl-2-oxo-decahydro-furo[3,2-e]indole-6-carboxylic acid methyl ester

(3aS,4R,5R,5aR,8aR,8bR)-4-Allyl-7-methoxy-5-[4-(4-methoxy-benzyloxy)-butyl]-2-oxo-decahydro-furo[3,2-e]indole-6-carboxylic acid methyl ester