(2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester
CAS No.:477351-67-0
Molecular Formula:C₄₀H₆₀N₂O₁₀Si
Molecular Weight:757.009
Hs Code.:

(2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

Synonyms:(2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

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Chemical Property of (2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

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Technology Process of (2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

There total 10 articles about (2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-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: 63.0%

: 477351-62-5
methyl (2S,5S,6S,3aR,7aS)-5,6-bis(methoxymethoxy)octahydroindole-2-carboxylate

: 477351-66-9
(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoic acid

: 477351-67-0
(2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

Guidance literature:: (R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoic acid; With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; In acetonitrile; at 0 ℃; for 1h;

methyl (2S,5S,6S,3aR,7aS)-5,6-bis(methoxymethoxy)octahydroindole-2-carboxylate; With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 24h; Further stages.;
DOI:10.1021/ja0208153

Reference yield:

: (2R,3S,4S,5R)-1,6-Bis-(tert-butyl-diphenyl-silanyloxy)-2,5-dimethoxy-hexane-3,4-diol

: 477351-67-0
(2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: Pd(OAc)4; Na₂CO₃ / CH₂Cl₂ / 2.5 h / 0 - 20 °C

2.1: 136 mg / NaClO₂; 2-methyl-2-butene; aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 0 - 20 °C

3.1: EDC; HOBt / DMAP / CH₂Cl₂ / 0.08 h / 0 °C

3.2: 95 percent / E₃N / CH₂Cl₂ / 0 - 20 °C

4.1: 99 percent / H₂ / Pd/C / methanol / 5 h / 760.05 Torr

5.1: BOPCl / acetonitrile / 1 h / 0 °C

5.2: 63 percent / DIEA / acetonitrile / 24 h / 20 °C

With palladium(II) acetate; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dmap; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja0208153

Reference yield:

: 148933-60-2
(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionaldehyde

: 477351-67-0
(2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 136 mg / NaClO₂; 2-methyl-2-butene; aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 0 - 20 °C

2.1: EDC; HOBt / DMAP / CH₂Cl₂ / 0.08 h / 0 °C

2.2: 95 percent / E₃N / CH₂Cl₂ / 0 - 20 °C

3.1: 99 percent / H₂ / Pd/C / methanol / 5 h / 760.05 Torr

4.1: BOPCl / acetonitrile / 1 h / 0 °C

4.2: 63 percent / DIEA / acetonitrile / 24 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dmap; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja0208153