(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

Base Information

• Chemical Name: (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
• CAS No.: 383863-71-6
• Molecular Formula: C₂₉H₄₁NO₇
• Molecular Weight: 515.647
• Mol file: 383863-71-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 23 articles about (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 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: 73.0%

(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 (383863-70-5) + methyl iodide (74-88-4) → (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 (383863-71-6)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1.) -78 deg C, 30 min, 2.) -78 deg C, 1.5 h;

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) → (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 (383863-71-6)

Guidance literature:

Multi-step reaction with 11 steps

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

1.2: 91.1 percent / hexane; tetrahydrofuran / 1.5 h / 0 °C

2.1: 100 percent / Et₃SiH / 10percent Pd/C / acetone / 1.5 h / 20 °C

3.1: 100 percent / aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C

4.1: diphenylphosphoryl azide; Et₃N / dimethylformamide / 0.5 h / 60 °C

5.1: 3.30 g / CuCl / dimethylformamide / 40 h / 20 °C

6.1: Et₃N; NaI / acetonitrile / 3 h / 50 °C

6.2: m-CPBA / hexane; CH₂Cl₂ / 2 h / -15 - 20 °C

7.1: aq. H₅IO₆ / tetrahydrofuran / 2 h / 20 °C

8.1: 2.93 g / I₂; NaHCO₃ / tetrahydrofuran / 40 h / 20 °C

9.1: 90 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 1 h / 20 °C

10.1: 80 percent / AIBN / toluene / 80 °C

11.1: LDA; HMPA / hexane; tetrahydrofuran / 0.5 h / -78 °C

11.2: 72.6 percent / hexane; tetrahydrofuran / 1.5 h / -78 °C

With triethylsilane; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; diphenylphosphoranyl azide; iodine; sodium hydrogencarbonate; periodic acid; triethylamine; sodium iodide; copper(l) chloride; lithium diisopropyl amide; 10percent Pd/C; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; 5.1: Curtius rearrangement;

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

Reference yield:

C36H45NO5S2 (177977-02-5) → (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 (383863-71-6)

Guidance literature:

Multi-step reaction with 12 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

5.1: diphenylphosphoryl azide; Et₃N / dimethylformamide / 0.5 h / 60 °C

6.1: 3.30 g / CuCl / dimethylformamide / 40 h / 20 °C

7.1: Et₃N; NaI / acetonitrile / 3 h / 50 °C

7.2: m-CPBA / hexane; CH₂Cl₂ / 2 h / -15 - 20 °C

8.1: aq. H₅IO₆ / tetrahydrofuran / 2 h / 20 °C

9.1: 2.93 g / I₂; NaHCO₃ / tetrahydrofuran / 40 h / 20 °C

10.1: 90 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 1 h / 20 °C

11.1: 80 percent / AIBN / toluene / 80 °C

12.1: LDA; HMPA / hexane; tetrahydrofuran / 0.5 h / -78 °C

12.2: 72.6 percent / hexane; tetrahydrofuran / 1.5 h / -78 °C

With triethylsilane; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; n-butyllithium; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; diphenylphosphoranyl azide; iodine; sodium hydrogencarbonate; silver nitrate; periodic acid; triethylamine; sodium iodide; copper(l) chloride; lithium diisopropyl amide; 10percent Pd/C; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; 6.1: Curtius rearrangement;

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

upstream raw materials:

(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

methyl iodide

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

(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

Downstream raw materials:

stenine