(2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-carboxylic acid (2R,3S)-((Z)-2-but-2-enyl)-tetrahydro-pyran-3-yl ester

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Chemical Name:(2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-carboxylic acid (2R,3S)-((Z)-2-but-2-enyl)-tetrahydro-pyran-3-yl ester
CAS No.:183722-20-5
Molecular Formula:C₂₂H₃₀O₅
Molecular Weight:374.477
Hs Code.:

Synonyms:(2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-carboxylic acid (2R,3S)-((Z)-2-but-2-enyl)-tetrahydro-pyran-3-yl ester

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Chemical Property of (2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-carboxylic acid (2R,3S)-((Z)-2-but-2-enyl)-tetrahydro-pyran-3-yl ester

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Technology Process of (2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-carboxylic acid (2R,3S)-((Z)-2-but-2-enyl)-tetrahydro-pyran-3-yl ester

There total 1 articles about (2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-carboxylic acid (2R,3S)-((Z)-2-but-2-enyl)-tetrahydro-pyran-3-yl 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: 81.0%

: (2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-carboxylic acid

: (2R,3S)-((Z)-2-But-2-enyl)-tetrahydro-pyran-3-ol

: 183722-20-5
(2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-carboxylic acid (2R,3S)-((Z)-2-but-2-enyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: With dmap; 2-chloromethylpyridinium iodide; triethylamine; In dichloromethane; at 25 ℃; for 3h;
DOI:10.1021/ja962862z

Reference yield: 50.0%

: 183722-20-5
(2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-carboxylic acid (2R,3S)-((Z)-2-but-2-enyl)-tetrahydro-pyran-3-yl ester

: 183722-21-6
(4aS,8aR)-6-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-2,3,4,4a,8,8a-hexahydro-pyrano[3,2-b]pyran

Guidance literature:: With Tebbe's reagent; In tetrahydrofuran; 1.) 25 deg C, 0.5 h, 2.) reflux, 4 h;
DOI:10.1021/ja962862z

Reference yield:

: 183722-20-5
(2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-carboxylic acid (2R,3S)-((Z)-2-but-2-enyl)-tetrahydro-pyran-3-yl ester

: (2S,3S,4aR,8aS)-2-((2S,3S)-3-Benzyloxy-tetrahydro-pyran-2-yl)-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 50 percent / μ-chloro-μ-methylene-dimethylaluminium / tetrahydrofuran / 1.) 25 deg C, 0.5 h, 2.) reflux, 4 h

2: 1.) BH₃, 2.) H₂O₂, 3 N aq. NaOH / 1.) THF, 0 deg C, 4 h, 2.) THF

With sodium hydroxide; Tebbe's reagent; borane; dihydrogen peroxide; In tetrahydrofuran;
DOI:10.1021/ja962862z