(2S,3S,4R,5R,6R)-4-Benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3S,4R,5R,6R)-4-Benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:356068-02-5
Molecular Formula:C₂₇H₃₄O₈
Molecular Weight:486.562
Hs Code.:

Synonyms:(2S,3S,4R,5R,6R)-4-Benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2S,3S,4R,5R,6R)-4-Benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2S,3S,4R,5R,6R)-4-Benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 12 articles about (2S,3S,4R,5R,6R)-4-Benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl 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: 57.0%

: 821-09-0
n-Pent-4-enyl alcohol

: 356067-97-5
(2S,3S,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester

: 356068-02-5
(2S,3S,4R,5R,6R)-4-Benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: (2S,3S,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester; In acetone; at 0 ℃;

n-Pent-4-enyl alcohol; With zinc(II) chloride; In dichloromethane;
DOI:10.1016/S0040-4039(01)00607-4

Reference yield:

: 356067-97-5
(2S,3S,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester

: 356068-02-5
(2S,3S,4R,5R,6R)-4-Benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: (2S,3S,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester; With DMDO; Further stages.;
DOI:10.1021/ja016227r

Reference yield:

: 2873-29-2
D-glucal triacetate

: 356068-02-5
(2S,3S,4R,5R,6R)-4-Benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaOMe / methanol

2.1: imidazole / dimethylformamide

3.1: Bu₂SnO / toluene

3.2: Bu₄NI

4.1: 77 percent / NaH / tetrahydrofuran

5.1: 95 percent / TBAF; AcOH / tetrahydrofuran

6.1: Dess-Martin periodinane / CH₂Cl₂

6.2: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol

7.1: 79 percent / KHCO₃ / dimethylformamide

8.1: DMDO / acetone / 0 °C

8.2: 57 percent / ZnCl₂ / CH₂Cl₂

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; di(n-butyl)tin oxide; potassium hydrogencarbonate; Dess-Martin periodane; acetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/S0040-4039(01)00607-4