1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL HYDROCHLORIDE

Base Information

• Chemical Name: 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL HYDROCHLORIDE
• CAS No.: 100991-92-2
• Molecular Formula: C5H12ClNO3
• Molecular Weight: 169.61
• Hs Code.: 2933990090
• Mol file: 100991-92-2.mol

Synonyms:1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL HYDROCHLORIDE

Chemical Property of 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL HYDROCHLORIDE

Chemical Property:

• Melting Point: 110-112 °C(Solv: ethyl ether (60-29-7); methanol (67-56-1))
• PSA: 72.72000
• LogP: -1.99890
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,4-Dideoxy-1,4-imino-D-arabinitol hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 1,4-dideoxy-1,4-imino-D-Arabinitol (DAB) is an inhibitor of glycogen phosphorylase, a key enzyme in glycogenolysis. It inhibits glycogenolysis in isolated liver cells (IC50 = 1.0 μM) and in homogenates of cerebral cortex and cerebellum (IC50s = 463 and 383 nM, respectively). DAB is used to inhibit glycogenolysis, in liver and in brain, in various animal models.
• Uses: 1,4-Dideoxy-1,4-imino-D-arabinitol hydrochloride has been used as an α-glucosidase (GAA) inhibitor.

Technology Process of 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL HYDROCHLORIDE

There total 39 articles about 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL HYDROCHLORIDE 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: 100.0%

(2R,3R,4R)-3,4-Dibenzyloxy-2-(benzyloxymethyl)pyrrolidine (135791-03-6) → (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine hydrochloride (100991-92-2)

Guidance literature:

With hydrogenchloride; 20% palladium hydroxide-activated charcoal; hydrogen; In water; isopropyl alcohol; at 20 ℃; for 48h;

DOI:10.1016/j.carres.2019.107855

Reference yield: 100.0%

2,3,5-tri-O-benzyl-1,4-benzylimino-1,4-dideoxy-D-arabinitol (909801-43-0) → (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine hydrochloride (100991-92-2)

Guidance literature:

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In ethanol; water; for 24h; Inert atmosphere;

DOI:10.1002/cmdc.201500407

Reference yield: 97.0%

(2R,3R,4R)-1-benzyloxycarbonyl-3,4-bis-benzyloxy-2-(hydroxymethyl)pyrrolidine → (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine hydrochloride (100991-92-2)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; for 24h; under 3102.89 Torr;

DOI:10.1021/ol061614x

upstream raw materials:

1,4-dideoxy-1,4-imino-D-arabitol

5-Azido-5-desoxy-D-xylulose

(2R,3R,4R)-N-benzyl-3,4-bis(benzyloxy)-2-hydroxymethylpyrrolidine

2,3,5-tri-O-benzyl-1,4-benzylimino-1,4-dideoxy-D-arabinitol

Downstream raw materials:

1,4-dideoxy-1,4-imino-D-arabitol

Refernces

• 1、 Jaszczyk, Justyna,Li, Sizhe,Cocaud, Chloé,Nicolas, Cyril,Martin, Olivier R.. "A practical approach to Dideoxy-1,4- and 1,5-iminopentitols from protected sugar hemiacetals". . . Retrieved 2019/11/11.
• 2、 Vandenberg, Richard J.B.H.N.,Vanrijssel, Erwin R.,Ferraz, Maria Joao,Houben, Judith,Strijland, Anneke,Donker-Koopman, Wilma E.,Wennekes, Tom,Bonger, Kimberly M.,Ghisaidoobe, Amar B. T.,Hoogendoorn, Sascha,Vandermarel, Gijsbert A.,Codée, Jeroen D. C.,Overkleeft, Herman S.,Aerts, Johannes M. F. G.. "Synthesis and Evaluation of Hybrid Structures Composed of Two Glucosylceramide Synthase Inhibitors". . p. 2042 - 2062. Retrieved 2015/12/23.