(2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

Base Information

Chemical Name:(2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester
CAS No.:264132-43-6
Molecular Formula:C₂₄H₃₅Cl₃O₅Si
Molecular Weight:537.983
Hs Code.:

Synonyms:(2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

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Chemical Property of (2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

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Technology Process of (2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

There total 5 articles about (2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl 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%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 264132-42-5
(2S,3S,6R)-6-[(1S)-1-hydroxyethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

: 264132-43-6
(2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 8h;
DOI:10.1021/jo991681n

Reference yield:

: 264132-38-9
(1R,2S)-[2-(p-methoxybenzyloxymethoxy)-1-ethenylpropoxy]acetic acid tert-butyl ester

: 264132-43-6
(2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: ozone; Ph₃P / CH₂Cl₂ / -78 °C

1.2: 65 percent / CuI; n-Bu₃P; BuLi / diethyl ether; tetrahydrofuran; hexane / 2 h / -78 °C

2.1: trifluoroacetic acid / benzene / 0.5 h / Heating

2.2: LiHMDS; Me₃SiCl; Et₃N / tetrahydrofuran / -78 °C

2.3: 89 percent / HCl / H₂O / pH 2

3.1: 92 percent / DMAP; DIC; TFA / CH₂Cl₂ / 40 °C

4.1: 82 percent / DDQ / H₂O; CH₂Cl₂ / 1 h

5.1: 96 percent / imidazole / dimethylformamide / 8 h / 20 °C

With 1H-imidazole; dmap; ozone; dacarbazine; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide; benzene; 1.1: Oxidation / 1.2: Addition / 2.1: Cyclization / 2.2: Rearrangement / 2.3: Hydrolysis / 3.1: Esterification / 4.1: Hydrolysis / 5.1: Etherification;
DOI:10.1021/jo991681n

Reference yield:

: 264132-40-3
(2S,3S,6R)-6-[(1S)-1-p-methoxybenzyloxymethoxyethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid

: 264132-43-6
(2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / DMAP; DIC; TFA / CH₂Cl₂ / 40 °C

2: 82 percent / DDQ / H₂O; CH₂Cl₂ / 1 h

3: 96 percent / imidazole / dimethylformamide / 8 h / 20 °C

With 1H-imidazole; dmap; dacarbazine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide; 1: Esterification / 2: Hydrolysis / 3: Etherification;
DOI:10.1021/jo991681n