(1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde

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-carbaldehyde
• CAS No.: 177977-14-9
• Molecular Formula: C₂₃H₃₀O₄
• Molecular Weight: 370.489
• Mol file: 177977-14-9.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-carbaldehyde

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-carbaldehyde

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-carbaldehyde

There total 13 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-carbaldehyde 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:

(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) → (1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde (177977-14-9)

Guidance literature:

With triethylsilane; lithium thioethoxide; palladium on activated charcoal; Yield given. Multistep reaction; 1.) THF, 0 deg C, 1.5 h, 2.) acetone, 0 deg C to r.t., 1 h;

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-carbaldehyde (177977-14-9)

Guidance literature:

Multi-step reaction with 4 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

4.1: 100 percent / Et₃SiH / 10percent Pd/C / acetone / 1.5 h / 20 °C

With triethylsilane; N-chloro-succinimide; n-butyllithium; dimethylaluminum chloride; silver nitrate; 10percent Pd/C; In tetrahydrofuran; hexane; dichloromethane; acetone; 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-carbaldehyde (177977-14-9)

Guidance literature:

Multi-step reaction with 3 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

3.1: 100 percent / Et₃SiH / 10percent Pd/C / acetone / 1.5 h / 20 °C

With triethylsilane; N-chloro-succinimide; n-butyllithium; silver nitrate; 10percent Pd/C; In tetrahydrofuran; hexane; acetone; 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

(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

1 ,5-pentanediol

Downstream raw materials:

stenine

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

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

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