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

Base Information

• Chemical Name: >-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2,4-pentadienyl>carbamic acid phenylmethyl ester
• CAS No.: 109215-73-8
• Molecular Formula: C₂₇H₄₇NO₄Si₂
• Molecular Weight: 505.845
• Mol file: 109215-73-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about >-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2,4-pentadienyl>carbamic acid phenylmethyl 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: 96.0%

t-butyldimethylsiyl triflate (69739-34-0) + >-<1-<1-<<(1,1-(dimethylethyl)dimethyl)silyl>oxy>ethyl>-4-oxo-2-pentenyl>carbamic acid phenylmethyl ester (109215-72-7) → >-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2,4-pentadienyl>carbamic acid phenylmethyl ester (109215-73-8)

Guidance literature:

With triethylamine; In benzene; at 50 ℃;

DOI:10.1016/S0040-4039(00)84109-X

Reference yield:

(2S,3R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate (104410-78-8) → >-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2,4-pentadienyl>carbamic acid phenylmethyl ester (109215-73-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 20percent DIBAL-H / toluene; hexane / 4 h / -78 °C

2: 80 percent / tetrahydrofuran / 24 h / Heating

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

With diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; toluene; benzene;

DOI:10.1021/ja00251a021

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → >-<4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>-2,4-pentadienyl>carbamic acid phenylmethyl ester (109215-73-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / 2N NaOH / 1 h / 0 °C

2: 99 percent / conc. sulfuric acid / 36 h / Ambient temperature

3: 99 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

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

5: 80 percent / tetrahydrofuran / 24 h / Heating

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

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

DOI:10.1021/ja00251a021

upstream raw materials:

t-butyldimethylsiyl triflate

>-<1-<1-<<(1,1-(dimethylethyl)dimethyl)silyl>oxy>ethyl>-4-oxo-2-pentenyl>carbamic acid phenylmethyl ester

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

N-benzyloxycarbonyl-L-treonine

Downstream raw materials:

2-[(1R,2R)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-6-[1-methoxycarbonyl-meth-(E)-ylidene]-cyclohex-3-enecarboxylic acid methyl ester

<3aS-(3aα,8α,9α,9aα,9bβ)>-(3a,4,8,9,9a,9b-hexahydro-5-hydroxy-2,2,8-trimethyl-6-oxo-6H-1,3-dioxolo<4,5-f><2>benzopyran-9-yl)carbamic acid phenylmethyl ester

[(3R,4R,4aS,5S,6S)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-yl]-carbamic acid benzyl ester

<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