N-Diphenylmethyl 2,5-Anhydro-2,5-imino-D-glucitol

Base Information

• Chemical Name: N-Diphenylmethyl 2,5-Anhydro-2,5-imino-D-glucitol
• CAS No.: 132198-31-3
• Molecular Formula: C₁₉H₂₃NO₄
• Molecular Weight: 329.396
• Mol file: 132198-31-3.mol

Synonyms:(2S,3R,4R,5R)-1-Benzhydryl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol

Chemical Property of N-Diphenylmethyl 2,5-Anhydro-2,5-imino-D-glucitol

Chemical Property:

• Boiling Point: 551.2±50.0 °C(Predicted)
• PKA: 13.54±0.70(Predicted)
• Density: 1.301±0.06 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

N-Diphenylmethyl 2,5-Anhydro-2,5-imino-D-glucitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Intermediate in the preparation of glycohydrolases inhibitors.

Technology Process of N-Diphenylmethyl 2,5-Anhydro-2,5-imino-D-glucitol

There total 3 articles about N-Diphenylmethyl 2,5-Anhydro-2,5-imino-D-glucitol 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: 28.0%

D-5-ketofructose (1684-29-3) + Benzhydrylamine (91-00-9) → N-Benzhydryl-2,5-anhydro-2,5-imino-D-mannitol (132198-33-5) + (2S,3R,4R,5R)-1-Benzhydryl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol (132198-31-3) + N-Benzhydryl-2,5-anhydro-2,5-imino-L-iditol (132198-32-4)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; for 6h; Heating;

DOI:10.1021/jo00090a040

Reference yield:

fructopyranose (6347-01-9) → (2S,3R,4R,5R)-1-Benzhydryl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol (132198-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: culture of Gluconobactor cerinus (ATCC catalogue number IFO 3267)

2: NaBH₄

With sodium tetrahydroborate; culture of Gluconobactor cerinus (ATCC catalogue number IFO 3267);

DOI:10.1039/a704885h

Reference yield:

D-5-ketofructose (1684-29-3) + Benzhydrylamine (91-00-9) → (2S,3R,4R,5R)-1-Benzhydryl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol (132198-31-3)

Guidance literature:

With sodium tetrahydroborate;

DOI:10.1039/a704885h

upstream raw materials:

D-5-ketofructose

Benzhydrylamine

fructopyranose

Downstream raw materials:

(4aS,6R,7R,7aR)-5-Benzhydryl-6-hydroxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol

(4aS,6R,7aR)-5-Benzhydryl-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxino[5,4-b]pyrrol-7-one

(2S,3R,4S,5R)-1-Benzhydryl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol

(4aS,6R,7S,7aR)-5-Benzhydryl-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol

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