(2R,4aR,7S,8R,8aR)-Hexahydro-7,8-dihydroxy-2-phenyl-5H-1,3-dioxino[5,4-b]pyridine-5-carboxylic Acid PhenylMethyl Ester

Base Information

• Chemical Name: (2R,4aR,7S,8R,8aR)-Hexahydro-7,8-dihydroxy-2-phenyl-5H-1,3-dioxino[5,4-b]pyridine-5-carboxylic Acid PhenylMethyl Ester
• CAS No.: 138381-83-6
• Molecular Formula: C21H23NO6
• Molecular Weight: 385.417
• Mol file: 138381-83-6.mol

Synonyms:(2R,4aR,7S,8R,8aR)-Hexahydro-7,8-dihydroxy-2-phenyl-5H-1,3-dioxino[5,4-b]pyridine-5-carboxylic Acid PhenylMethyl Ester;N-Benzyloxycarbonyl-4,6-O-phenylMethylene DeoxynojiriMycin

Chemical Property of (2R,4aR,7S,8R,8aR)-Hexahydro-7,8-dihydroxy-2-phenyl-5H-1,3-dioxino[5,4-b]pyridine-5-carboxylic Acid PhenylMethyl Ester

Chemical Property:

• PSA: 88.46000
• LogP: 1.78130

Purity/Quality:

99% ^*data from raw suppliers

N-Benzyloxycarbonyl-4,6-O-phenylmethylene Deoxynojirimycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Deoxynojirimycin (D245000) derivative. Reactant in the preparation of sialoglycoconjugates.

Technology Process of (2R,4aR,7S,8R,8aR)-Hexahydro-7,8-dihydroxy-2-phenyl-5H-1,3-dioxino[5,4-b]pyridine-5-carboxylic Acid PhenylMethyl Ester

There total 7 articles about (2R,4aR,7S,8R,8aR)-Hexahydro-7,8-dihydroxy-2-phenyl-5H-1,3-dioxino[5,4-b]pyridine-5-carboxylic Acid PhenylMethyl 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: 84.0%

N-Benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol (130539-12-7) + benzaldehyde dimethyl acetal (1125-88-8) → 4,6-O-(R-Benzylidene)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol (138381-83-6)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1002/chem.201002313

Reference yield: 54.0%

1,5-Dideoxy-1,5-[[(2-methoxyethoxy)carbonyl]imino]-3-S-phenyl-4,6-O-(R-phenylmethylene)-3-thio-D-altritol + benzaldehyde dimethyl acetal (1125-88-8) → 4,6-O-(R-Benzylidene)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol (138381-83-6)

Guidance literature:

With sodium hydrogencarbonate; toluene-4-sulfonic acid; In ice-water; hexane; water; ethyl acetate;

Reference yield:

1,5-dideoxy-1,5-imino-D-glucitol (19130-96-2) → 4,6-O-(R-Benzylidene)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol (138381-83-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / Na₂CO₃ / H₂O

2: 65 percent / TosOH

With sodium carbonate; toluene-4-sulfonic acid; In water;

DOI:10.1016/0040-4039(96)00021-4

upstream raw materials:

N-Benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol

benzaldehyde

1,5-dideoxy-1,5-imino-D-glucitol

benzyl chloroformate

Downstream raw materials:

2-O-acetyl-4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol

(4aR,7S,8R,8aR)-8-Acetoxy-7-hydroxy-2-phenyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid benzyl ester

(4aR,7S,8R,8aR)-8-Butyryloxy-7-hydroxy-2-phenyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid benzyl ester

(4aR,7S,8R,8aR)-7-Butyryloxy-8-hydroxy-2-phenyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid benzyl ester