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

Base Information

Chemical Name:(2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid
CAS No.:264132-44-7
Molecular Formula:C₂₂H₃₄O₅Si
Molecular Weight:406.594
Hs Code.:

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

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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

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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

There total 7 articles about (2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-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: 100.0%

: 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

: 264132-44-7
(2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid

Guidance literature:: With lithium hydroxide; In water; tert-butyl alcohol; for 2h;
DOI:10.1021/jo991681n

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 264132-44-7
(2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / imidazole / dimethylformamide / 8 h / 20 °C

2: 100 percent / lithium hydroxide / 2-methyl-propan-2-ol; H₂O / 2 h

With 1H-imidazole; lithium hydroxide; In water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Etherification / 2: Hydrolysis;
DOI:10.1021/jo991681n

Reference yield:

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

: 264132-44-7
(2S,3S,6R)-6-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3-benzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 6 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

6.1: 100 percent / lithium hydroxide / 2-methyl-propan-2-ol; H₂O / 2 h

With 1H-imidazole; dmap; lithium hydroxide; ozone; dacarbazine; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 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 / 6.1: Hydrolysis;
DOI:10.1021/jo991681n