(2R,3S,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(2R,3S,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid benzyl ester
CAS No.:131429-65-7
Molecular Formula:C₁₇H₂₄O₄
Molecular Weight:292.375
Hs Code.:

Synonyms:(2R,3S,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid benzyl ester

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Chemical Property of (2R,3S,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid benzyl ester

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Technology Process of (2R,3S,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 3 articles about (2R,3S,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid benzyl 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: 97.0%

: 131429-90-8
(2R,3S,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid

: 100-51-6,185532-71-2
benzyl alcohol

: 131429-65-7
(2R,3S,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: With dmap; 4-N,N-dimethylaminopyridine trifluoroacetate; dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃;
DOI:10.1016/S0040-4039(00)98051-1

Reference yield:

: 96720-60-4,107134-01-0,131487-83-7
(5R,6R)-5-((R)-2-Benzyloxy-1-methyl-ethyl)-6-((E)-propenyl)-[1,4]dioxan-2-one

: 131429-65-7
(2R,3S,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1) LiHMDS, TMSCl/Et₃N, 2) aq. 5percent HCl / 1) THF, -78 deg C, then reflux, 4.5 h

2: 96 percent / H₂ / Pd/C / ethanol / 10 h / 760 Torr / Ambient temperature

3: 97 percent / DCC, DMAP, DMAP-TFA / CH₂Cl₂ / 25 °C

With hydrogenchloride; dmap; chloro-trimethyl-silane; hydrogen; 4-N,N-dimethylaminopyridine trifluoroacetate; triethylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; palladium on activated charcoal; In ethanol; dichloromethane;
DOI:10.1016/S0040-4039(00)98051-1

Reference yield:

: 131429-89-5
(2R,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-3,6-dihydro-2H-pyran-2-carboxylic acid

: 131429-65-7
(2R,3S,6S)-6-((R)-2-Hydroxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / H₂ / Pd/C / ethanol / 10 h / 760 Torr / Ambient temperature

2: 97 percent / DCC, DMAP, DMAP-TFA / CH₂Cl₂ / 25 °C

With dmap; hydrogen; 4-N,N-dimethylaminopyridine trifluoroacetate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; dichloromethane;
DOI:10.1016/S0040-4039(00)98051-1