(2S,3S,6R)-6-[(1S)-1-hydroxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

Base Information

Chemical Name:(2S,3S,6R)-6-[(1S)-1-hydroxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester
CAS No.:264132-33-4
Molecular Formula:C₁₉H₂₃Cl₃O₆
Molecular Weight:453.747
Hs Code.:

Synonyms:(2S,3S,6R)-6-[(1S)-1-hydroxyethyl]-3-p-methoxybenzyloxymethyl-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-hydroxyethyl]-3-p-methoxybenzyloxymethyl-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-hydroxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

There total 6 articles about (2S,3S,6R)-6-[(1S)-1-hydroxyethyl]-3-p-methoxybenzyloxymethyl-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: 82.0%

: 264132-31-2
(2S,3S,6R)-6-[(1S)-1-benzyloxymethoxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

: 264132-33-4
(2S,3S,6R)-6-[(1S)-1-hydroxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

Guidance literature:: With dimethylsulfide; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.166667h;
DOI:10.1021/jo991681n

Reference yield:

: ((1S,2S)-2-Benzyloxymethoxy-1-formyl-propoxy)-acetic acid tert-butyl ester

: 264132-33-4
(2S,3S,6R)-6-[(1S)-1-hydroxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 69 percent / CuI; n-Bu₃P; PhLi / tetrahydrofuran; diethyl ether / -78 °C

2.1: trifluoroacetic acid / benzene / 0.5 h / Heating

3.1: LiHMDS; Me₃SiCl; Et₃N / hexane; tetrahydrofuran / 2 h / -78 °C

3.2: HCl / H₂O / pH 2

4.1: 95 percent / DMAP; DIC; TFA / CH₂Cl₂ / 40 °C

5.1: 82 percent / BF₃-Et₂O; Me₂S / CH₂Cl₂ / 0.17 h / 0 °C

With dmap; copper(l) iodide; chloro-trimethyl-silane; dimethylsulfide; tributylphosphine; boron trifluoride diethyl etherate; phenyllithium; dacarbazine; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene; 1.1: Addition / 2.1: Cyclization / 3.1: Rearrangement / 3.2: Hydrolysis / 4.1: Esterification / 5.1: Hydrolysis;
DOI:10.1021/jo991681n

Reference yield:

: Tributyl-[(E)-3-(4-methoxy-benzyloxy)-propenyl]-stannane

: 264132-33-4
(2S,3S,6R)-6-[(1S)-1-hydroxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid 2,2,2-trichloroethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 69 percent / CuI; n-Bu₃P; PhLi / tetrahydrofuran; diethyl ether / -78 °C

2.1: trifluoroacetic acid / benzene / 0.5 h / Heating

3.1: LiHMDS; Me₃SiCl; Et₃N / hexane; tetrahydrofuran / 2 h / -78 °C

3.2: HCl / H₂O / pH 2

4.1: 95 percent / DMAP; DIC; TFA / CH₂Cl₂ / 40 °C

5.1: 82 percent / BF₃-Et₂O; Me₂S / CH₂Cl₂ / 0.17 h / 0 °C

With dmap; copper(l) iodide; chloro-trimethyl-silane; dimethylsulfide; tributylphosphine; boron trifluoride diethyl etherate; phenyllithium; dacarbazine; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene; 1.1: Addition / 2.1: Cyclization / 3.1: Rearrangement / 3.2: Hydrolysis / 4.1: Esterification / 5.1: Hydrolysis;
DOI:10.1021/jo991681n