(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

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
CAS No.:477351-80-7
Molecular Formula:C₃₉H₅₈N₂O₁₀Si
Molecular Weight:742.982
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

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

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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

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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

There total 12 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 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: 97.0%

: 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

: 477351-80-7
(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

Guidance literature:: With lithium hydroxide; In tetrahydrofuran;
DOI:10.1021/ja0208153

Reference yield:

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

: 477351-80-7
(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

Guidance literature:: Multi-step reaction with 6 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

6.1: 97 percent / aq. LiOH / tetrahydrofuran

With palladium(II) acetate; lithium hydroxide; 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 tetrahydrofuran; methanol; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja0208153

Reference yield:

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

: 477351-80-7
(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

Guidance literature:: Multi-step reaction with 5 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

5.1: 97 percent / aq. LiOH / tetrahydrofuran

With lithium hydroxide; 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 tetrahydrofuran; methanol; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja0208153