5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal

Base Information

• Chemical Name: 5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal
• CAS No.: 188242-61-7
• Molecular Formula: C₁₉H₂₉NO₇
• Molecular Weight: 383.442
• Mol file: 188242-61-7.mol

Synonyms:5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal

Chemical Property of 5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal

There total 2 articles about 5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal 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:

(3R,4R,5R,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester (173829-12-4) → 5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal (188242-61-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Amberlyst-15 (H⁺) / 2 h / 40 °C

2: H₂ / Pd/C / ethanol / 24 h / 50 °C

3: 1.55 g / NaOH / H₂O / 3 h / 20 °C

With sodium hydroxide; Amberlyst-15 (H⁺); hydrogen; palladium on activated charcoal; In ethanol; water; 1: Substitution / 2: Catalytic hydrogenation / 3: Substitution;

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

Reference yield:

benzyl (3R)-t-4,t-5-isopropylidenedioxy-c-6-dimethoxymethyl-r-3-methyl-1,2-oxazane-2-carboxylate (188242-60-6) → 5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal (188242-61-7)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / ethanol / 24 h / 50 °C

2: 1.55 g / NaOH / H₂O / 3 h / 20 °C

With sodium hydroxide; hydrogen; palladium on activated charcoal; In ethanol; water; 1: Catalytic hydrogenation / 2: Substitution;

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

Reference yield: 100.0%

methanesulfonyl chloride (124-63-0) + 5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal (188242-61-7) → 5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-2-O-methanesulfonyl-5,6-dideoxy-D-allose dimethylacetal (188242-63-9)

Guidance literature:

With triethylamine; In dichloromethane; at -10 ℃; for 1h;

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

upstream raw materials:

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

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

Downstream raw materials:

5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-2-O-methanesulfonyl-5,6-dideoxy-D-allose dimethylacetal

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

(2S,3S,4R,5R)-3,4-dihydroxy-2-hydroxymethyl-5-methylpyrrolidine

(2R,3S,4R,5R)-2-(hydroxymethyl)-5-methylpyrrolidine-3,4-diol