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

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-carboxylic acid
• CAS No.: 177977-04-7
• Molecular Formula: C₂₃H₃₀O₅
• Molecular Weight: 386.488

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

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-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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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-carboxylic acid

There total 15 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-carboxylic acid 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: 100.0%

(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) → (1R,2R,4aS,8aR)-2-[4-(4-Methoxy-benzyloxy)-butyl]-6-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid (177977-04-7)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; for 1h;

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-carboxylic acid (177977-04-7)

Guidance literature:

Multi-step reaction with 5 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

5.1: 100 percent / aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

With triethylsilane; sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; n-butyllithium; 2-methyl-but-2-ene; dimethylaluminum chloride; silver nitrate; 10percent Pd/C; In tetrahydrofuran; hexane; dichloromethane; acetone; acetonitrile; tert-butyl alcohol; 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-carboxylic acid (177977-04-7)

Guidance literature:

Multi-step reaction with 4 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

4.1: 100 percent / aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

With triethylsilane; sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; n-butyllithium; 2-methyl-but-2-ene; silver nitrate; 10percent Pd/C; In tetrahydrofuran; hexane; acetone; acetonitrile; tert-butyl alcohol;

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

upstream raw materials:

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

(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

Downstream raw materials:

{(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

stenine

(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

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