(2R,4R,5R,6S)-4-Benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester

Base Information

Chemical Name:(2R,4R,5R,6S)-4-Benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester
CAS No.:186831-58-3
Molecular Formula:C₁₇H₂₂O₈
Molecular Weight:354.357
Hs Code.:

Synonyms:(2R,4R,5R,6S)-4-Benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester

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Chemical Property of (2R,4R,5R,6S)-4-Benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester

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Technology Process of (2R,4R,5R,6S)-4-Benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester

There total 8 articles about (2R,4R,5R,6S)-4-Benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl 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:

: 100-39-0
benzyl bromide

: 186831-58-3
(2R,4R,5R,6S)-4-Benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 71 percent / Ag₂O / acetonitrile; dimethylformamide / Ambient temperature

2: 93 percent / CSA / CH₂Cl₂; methanol / 1 h / Ambient temperature

3: 1.) aq. NaHCO₃, KBr, TEMPO, NaOCl, 2.) 1M Me₃SiCl / 1.) CH₂Cl₂, 1 h, 0 deg C; 2.) CH₂Cl₂

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; chloro-trimethyl-silane; camphor-10-sulfonic acid; sodium hydrogencarbonate; potassium bromide; silver(l) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0008-6215(97)10073-8

Reference yield:

: 85549-53-7,85549-51-5
(2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 186831-58-3
(2R,4R,5R,6S)-4-Benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / CSA / dimethylformamide / 3 h / Ambient temperature

2: 71 percent / Ag₂O / acetonitrile; dimethylformamide / Ambient temperature

3: 93 percent / CSA / CH₂Cl₂; methanol / 1 h / Ambient temperature

4: 1.) aq. NaHCO₃, KBr, TEMPO, NaOCl, 2.) 1M Me₃SiCl / 1.) CH₂Cl₂, 1 h, 0 deg C; 2.) CH₂Cl₂

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; chloro-trimethyl-silane; camphor-10-sulfonic acid; sodium hydrogencarbonate; potassium bromide; silver(l) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0008-6215(97)10073-8

Reference yield:

: (2R,4R,5R,6R)-4-Hydroxy-5-isopropoxy-6-isopropoxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 186831-58-3
(2R,4R,5R,6S)-4-Benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 71 percent / Ag₂O / acetonitrile; dimethylformamide / Ambient temperature

2: 93 percent / CSA / CH₂Cl₂; methanol / 1 h / Ambient temperature

3: 1.) aq. NaHCO₃, KBr, TEMPO, NaOCl, 2.) 1M Me₃SiCl / 1.) CH₂Cl₂, 1 h, 0 deg C; 2.) CH₂Cl₂

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; chloro-trimethyl-silane; camphor-10-sulfonic acid; sodium hydrogencarbonate; potassium bromide; silver(l) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0008-6215(97)10073-8