benzyl (3R)-c-4,c-5-isopropylidenedioxy-c-6-dimethoxymethyl-r-3-methyl-1,2-oxazane-2-carboxylate

Base Information

• Chemical Name: benzyl (3R)-c-4,c-5-isopropylidenedioxy-c-6-dimethoxymethyl-r-3-methyl-1,2-oxazane-2-carboxylate
• CAS No.: 264234-38-0
• Molecular Formula: C₁₉H₂₇NO₇
• Molecular Weight: 381.426
• Mol file: 264234-38-0.mol

Synonyms:benzyl (3R)-c-4,c-5-isopropylidenedioxy-c-6-dimethoxymethyl-r-3-methyl-1,2-oxazane-2-carboxylate

Chemical Property of benzyl (3R)-c-4,c-5-isopropylidenedioxy-c-6-dimethoxymethyl-r-3-methyl-1,2-oxazane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (3R)-c-4,c-5-isopropylidenedioxy-c-6-dimethoxymethyl-r-3-methyl-1,2-oxazane-2-carboxylate

There total 1 articles about benzyl (3R)-c-4,c-5-isopropylidenedioxy-c-6-dimethoxymethyl-r-3-methyl-1,2-oxazane-2-carboxylate 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: 67.0%

2,2-dimethoxy-propane (77-76-9) + (3R,4S,5S,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester (173933-53-4) → benzyl (3R)-c-4,c-5-isopropylidenedioxy-c-6-dimethoxymethyl-r-3-methyl-1,2-oxazane-2-carboxylate (264234-38-0)

Guidance literature:

With Amberlyst-15 (H⁺); at 45 ℃; for 5h;

DOI:10.1016/S0040-4020(99)01078-9

Reference yield:

benzyl (3R)-c-4,c-5-isopropylidenedioxy-c-6-dimethoxymethyl-r-3-methyl-1,2-oxazane-2-carboxylate (264234-38-0) → 2,5-(benzyloxycarbonylimino)-2,5,6-trideoxy-D-talitol (264234-43-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / H₂ / Pd/C / ethanol / 14 h / 50 °C

2: 1.68 g / NaOH / H₂O / 4.5 h / 20 °C

3: 100 percent / Et₃N / CH₂Cl₂ / 1 h / -10 °C

4: 1.17 g / NaOH / ethanol; H₂O / 14 h / 80 °C

5: Amberlyst-15 (H⁺) / acetone / 17.5 h / 40 °C

6: 0.58 g / NaBH₄ / methanol / 20 °C

7: 92 percent / Amberlyst-15 (H⁺) / ethanol / 4 h / 80 °C

With sodium hydroxide; sodium tetrahydroborate; Amberlyst-15 (H⁺); hydrogen; triethylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; acetone; 1: Catalytic hydrogenation / 2: Substitution / 3: Substitution / 4: Cyclization / 5: Acetal removing / 6: Reduction / 7: Substitution;

DOI:10.1016/S0040-4020(99)01078-9

Reference yield:

benzyl (3R)-c-4,c-5-isopropylidenedioxy-c-6-dimethoxymethyl-r-3-methyl-1,2-oxazane-2-carboxylate (264234-38-0) → 2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-talitol (264234-49-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / H₂ / Pd/C / ethanol / 14 h / 50 °C

2: 1.68 g / NaOH / H₂O / 4.5 h / 20 °C

3: 100 percent / Et₃N / CH₂Cl₂ / 1 h / -10 °C

4: 1.17 g / NaOH / ethanol; H₂O / 14 h / 80 °C

5: Amberlyst-15 (H⁺) / acetone / 17.5 h / 40 °C

6: 0.58 g / NaBH₄ / methanol / 20 °C

With sodium hydroxide; sodium tetrahydroborate; Amberlyst-15 (H⁺); hydrogen; triethylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; acetone; 1: Catalytic hydrogenation / 2: Substitution / 3: Substitution / 4: Cyclization / 5: Acetal removing / 6: Reduction;

DOI:10.1016/S0040-4020(99)01078-9

upstream raw materials:

2,2-dimethoxy-propane

(3R,4S,5S,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester

Downstream raw materials:

(1R,2S,3R,4R)-1-methyl-2,3-diol-4-hydroxymethyl pyrrolidine

2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-talose

2,5-(benzyloxycarbonylimino)-2,5,6-trideoxy-D-talitol

2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-talitol