(2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid methoxy-methyl-amide

Base Information

Chemical Name:(2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid methoxy-methyl-amide
CAS No.:263006-25-3
Molecular Formula:C₂₂H₂₇NO₅
Molecular Weight:385.46
Hs Code.:

Synonyms:(2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid methoxy-methyl-amide

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Chemical Property of (2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid methoxy-methyl-amide

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Technology Process of (2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid methoxy-methyl-amide

There total 4 articles about (2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid methoxy-methyl-amide 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: 85.0%

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 263006-24-2
(2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid

: 263006-25-3
(2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid methoxy-methyl-amide

Guidance literature:: (2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid; In dichloromethane; for 5h; Heating;

N,O-dimethylhydroxylamine*hydrochloride; With triethylamine; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1016/S0040-4039(99)02078-X

Reference yield:

: 452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3
D-2-deoxyribose

: 263006-25-3
(2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 3 steps

1.1: AcCl; Ag₂CO₃ / methanol / 0.12 h / 20 °C

1.2: NaH; Bu₄NI / dimethylformamide / 24 h / -30 - 20 °C

1.3: TMSOTf / CH₂Cl₂ / 24 h / 20 °C

2.1: 100 percent / HCl / dioxane / 4 h / 100 °C

3.1: α,α-dichloromethylmethyl ether / CH2Cl2 / 5 h / Heating

3.2: 85 percent / NEt₃ / CH₂Cl₂ / 24 h / 20 °C

With hydrogenchloride; acetyl chloride; silver carbonate; In 1,4-dioxane; methanol; dichloromethane; 1.1: Acetylation / 1.2: Etherification / 1.3: Substitution / 2.1: Hydrolysis / 3.1: activation / 3.2: Substitution;
DOI:10.1016/S0040-4039(99)02078-X

Reference yield:

: 100-39-0
benzyl bromide

: 263006-25-3
(2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carboxylic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 3 steps

1.1: AcCl; Ag₂CO₃ / methanol / 0.12 h / 20 °C

1.2: NaH; Bu₄NI / dimethylformamide / 24 h / -30 - 20 °C

1.3: TMSOTf / CH₂Cl₂ / 24 h / 20 °C

2.1: 100 percent / HCl / dioxane / 4 h / 100 °C

3.1: α,α-dichloromethylmethyl ether / CH2Cl2 / 5 h / Heating

3.2: 85 percent / NEt₃ / CH₂Cl₂ / 24 h / 20 °C

With hydrogenchloride; acetyl chloride; silver carbonate; In 1,4-dioxane; methanol; dichloromethane; 1.1: Acetylation / 1.2: Etherification / 1.3: Substitution / 2.1: Hydrolysis / 3.1: activation / 3.2: Substitution;
DOI:10.1016/S0040-4039(99)02078-X