(R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester

Base Information

• Chemical Name: (R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester
• CAS No.: 104486-64-8
• Molecular Formula: C₃₁H₅₁NO₆Si₂
• Molecular Weight: 589.92

Synonyms:(R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester

Chemical Property of (R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester

There total 8 articles about (R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic 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: 55.0%

>-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2,4-pentadienyl>carbamic acid phenylmethyl ester (109215-73-8) + propynoic acid methyl ester (922-67-8) → (R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester (104486-64-8) + (S)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester (104410-81-3)

Guidance literature:

at 220 ℃; for 0.5h; sealed tube;

DOI:10.1021/ja00251a021

Reference yield: 21.0%

>-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2,4-pentadienyl>carbamic acid phenylmethyl ester (109215-73-8) + propynoic acid methyl ester (922-67-8) → >-<1-<1-<<(1,1-(dimethylethyl)dimethyl)silyl>oxy>ethyl>-4-oxo-2-pentenyl>carbamic acid phenylmethyl ester (109215-72-7) + (R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester (104486-64-8) + (S)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester (104410-81-3)

Guidance literature:

In benzene; at 110 ℃; for 24h; sealed tube;

DOI:10.1021/ja00251a021

Reference yield:

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate (57224-63-2) → (R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,4-dienecarboxylic acid methyl ester (104486-64-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

2: 20percent DIBAL-H / toluene; hexane / 4 h / -78 °C

3: 80 percent / tetrahydrofuran / 24 h / Heating

4: 96 percent / triethylamine / benzene / 1.) 0 deg C, 5 min, 2.) RT, 15 min, 3.) 55 deg C, 6 h

5: 21 percent / benzene / 24 h / 110 °C / sealed tube

With 1H-imidazole; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00251a021

upstream raw materials:

>-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2,4-pentadienyl>carbamic acid phenylmethyl ester

propynoic acid methyl ester

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate

N-benzyloxycarbonyl-L-treonine

Downstream raw materials:

<3R-(3α,4α,4aβ,5β,6α)>-(3,4,4a,5,6,7-hexahydro-5,6-dihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl)carbamic acid phenylmethyl ester

(4R,5R,6R)-6-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

<4R-<4α,5β,6α(1R*,2R*)>>-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-6-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<<(phenylmethoxy)carbonyl>amino>propyl>-5-hydroxy-1-cyclohexene-1-carboxylic acid methyl ester

<1aR-(1aα,3α,4β,4aβ,5α,6α,6α,8aS*)>-(hexahydro-3,4-dihydroxy-6-methyl-8-oxo-3H,8H-oxireno<2>benzopyran-5-yl)carbamic acid phenylmethyl ester

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