(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

Base Information

Chemical Name:(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
CAS No.:383863-69-2
Molecular Formula:C₂₅H₃₄INO₇
Molecular Weight:587.452
Hs Code.:

Synonyms:(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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Chemical Property of (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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Technology Process of (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

There total 21 articles about (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 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: 90.0%

: 383863-68-1
(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

: 149-73-5
trimethyl orthoformate

: 383863-69-2
(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

Guidance literature:: With camphor-10-sulfonic acid; In methanol; dichloromethane; for 1h; Ambient temperature;

Reference yield:

: 177977-03-6
(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

: 383863-69-2
(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

Guidance literature:: Multi-step reaction with 9 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

With triethylsilane; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; camphor-10-sulfonic acid; diphenylphosphoranyl azide; iodine; sodium hydrogencarbonate; periodic acid; triethylamine; sodium iodide; copper(l) chloride; 10percent Pd/C; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 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:

: 177977-02-5
C₃₆H₄₅NO₅S₂

: 383863-69-2
(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

Guidance literature:: Multi-step reaction with 10 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

With triethylsilane; sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; n-butyllithium; 2-methyl-but-2-ene; camphor-10-sulfonic acid; diphenylphosphoranyl azide; iodine; sodium hydrogencarbonate; silver nitrate; periodic acid; triethylamine; sodium iodide; copper(l) chloride; 10percent Pd/C; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; 6.1: Curtius rearrangement;
DOI:10.1002/1521-3765(20011001)7:19<4107::AID-CHEM4107>3.0.CO;2-K