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

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Chemical Name:(2S,3S,6R)-6-[(1S)-1-benzyloxymethoxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid
CAS No.:264132-29-8
Molecular Formula:C₂₅H₃₀O₇
Molecular Weight:442.509
Hs Code.:

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

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Chemical Property of (2S,3S,6R)-6-[(1S)-1-benzyloxymethoxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid

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Technology Process of (2S,3S,6R)-6-[(1S)-1-benzyloxymethoxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid

There total 4 articles about (2S,3S,6R)-6-[(1S)-1-benzyloxymethoxyethyl]-3-p-methoxybenzyloxymethyl-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:

: 1055029-11-2
(5S,6S)-5-((S)-1-Benzyloxymethoxy-ethyl)-6-[(E)-3-(4-methoxy-benzyloxy)-propenyl]-[1,4]dioxan-2-one

: 264132-29-8
(2S,3S,6R)-6-[(1S)-1-benzyloxymethoxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid

Guidance literature:: (5S,6S)-5-((S)-1-Benzyloxymethoxy-ethyl)-6-[(E)-3-(4-methoxy-benzyloxy)-propenyl]-[1,4]dioxan-2-one; With chloro-trimethyl-silane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

With hydrogenchloride; In water; pH=2; Further stages.;
DOI:10.1021/jo991681n

Reference yield:

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

: 264132-29-8
(2S,3S,6R)-6-[(1S)-1-benzyloxymethoxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 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

With copper(l) iodide; chloro-trimethyl-silane; tributylphosphine; phenyllithium; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; benzene; 1.1: Addition / 2.1: Cyclization / 3.1: Rearrangement / 3.2: Hydrolysis;
DOI:10.1021/jo991681n

Reference yield:

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

: 264132-29-8
(2S,3S,6R)-6-[(1S)-1-benzyloxymethoxyethyl]-3-p-methoxybenzyloxymethyl-3,6-dihydro-2H-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 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

With copper(l) iodide; chloro-trimethyl-silane; tributylphosphine; phenyllithium; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; benzene; 1.1: Addition / 2.1: Cyclization / 3.1: Rearrangement / 3.2: Hydrolysis;
DOI:10.1021/jo991681n