1,4-Dideoxy-1,4-imino-D-mannitol hydrochloride

Base Information

• Chemical Name: 1,4-Dideoxy-1,4-imino-D-mannitol hydrochloride
• CAS No.: 114976-76-0
• Molecular Formula: C6H13 N O4 . Cl H
• Molecular Weight: 199.634
• Hs Code.: 29389090
• European Community (EC) Number: 631-220-0
• ChEMBL ID: CHEMBL2374730
• Mol file: 114976-76-0.mol

Synonyms:114976-76-0;1,4-DIDEOXY-1,4-IMINO-D-MANNITOL HYDROCHLORIDE;1,4-Dideoxy-1,4-imino-D-mannitol, Hydrochloride;(2R,3S,4R)-2-((S)-1,2-Dihydroxyethyl)pyrrolidine-3,4-diol hydrochloride;(2R,3S,4R)-2-[(1S)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol;hydrochloride;SCHEMBL960466;CHEMBL2374730;3,4-Pyrrolidinediol, 2-[(1S)-1,2-dihydroxyethyl]-, hydrochloride, (2R,3S,4R)-;(2R,3S,4R)-2-[(1S)-1,2-Dihydroxyethyl]-3,4-pyrrolidinediol Hydrochloride;AKOS006277596;W-200870;1,4-Dideoxy-1,4-imino-D-mannitol hydrochloride, >=90% (HPLC);(2S,3S,4R)-2-[(1S)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol hydrochloride

Chemical Property of 1,4-Dideoxy-1,4-imino-D-mannitol hydrochloride

Chemical Property:

• Melting Point: 147-148°C
• Boiling Point: 448.6°Cat760mmHg
• Flash Point: 258°C
• PSA: 92.95000
• Density: 1.492g/cm³
• LogP: -1.83600
• Storage Temp.: 2-8°C
• Solubility.: Water
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 199.0611356
• Heavy Atom Count: 12
• Complexity: 132

Purity/Quality:

98% ^*data from raw suppliers

1,4-Dideoxy-1,4-imino-D-mannitol HCl ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(N1)C(CO)O)O)O.Cl
• Isomeric SMILES: C1[C@H]([C@H]([C@H](N1)[C@@H](CO)O)O)O.Cl
• Uses: A competitive glycosidase inhibitor. It is also a glycoprotein mannosidase inhibitor - inhibiting jack bean, and to a lesser extent lysosomal alpha-mannosidase. It is an azofuranose analog of mannose, and is structurally related to swainsonine. A competitive glycosidase inhibitor. It is also a glycoprotein mannosidase inhibitor - inhibiting jack bean, and to a lesser extent lysosomal alpha-mannosidase. It is an azofuranose analog of mannose, and is structurally related to swainsonine

Technology Process of 1,4-Dideoxy-1,4-imino-D-mannitol hydrochloride

There total 19 articles about 1,4-Dideoxy-1,4-imino-D-mannitol 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%

(S)-1-[(3aS,4R,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-2-methoxymethoxy-ethanol (180182-35-8) → 1,4-dideoxy-1,4-imino-D-mannitol hydrochloride (114976-76-0)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In methanol; for 13h; under 2689.2 Torr;

DOI:10.1021/jo9604245

Reference yield: 96.0%

(S)-1-((3aS,4R,6aR)-5-benzyl-2,2-dimethyltetrahydro-4H-[1,3] dioxolo[4,5-c]pyrrol-4-yl)ethane-1,2-diol (851390-80-2) → 1,4-dideoxy-1,4-imino-D-mannitol hydrochloride (114976-76-0)

Guidance literature:

With hydrogenchloride; hydrogen; palladium dihydroxide; In methanol; for 24h; under 2280 Torr;

DOI:10.1055/s-2005-861792

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 1,4-dideoxy-1,4-imino-D-mannitol hydrochloride (114976-76-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) chlorotrimethylsilane, Et₃N, 2.) Et₃N, Pb(NO₃)2 / 1) CH₂Cl₂, reflux, 1 h; 2) CH₂Cl₂, MeOH, rt, 96 h

2: 100 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -60 °C

3: 1.) NaHMDS, 2.) MoOPH / 1) THF, -78 deg C, 2 h; 2) THF, -78 - -15 deg C, 2.5 h

4: 92 percent / NaBH₄ / methanol; tetrahydrofuran / 4 h / -78 °C

5: 97 percent / PPTS / dimethylformamide; acetone / 24 h / 5 °C

6: 1.) n-BuLi, 2.) LiClO₄ / 1) hexane, THF, -78 - -65 deg C, 5 min; 2) THF, hexane, -78 deg C, 2 h

7: 100 percent / LiEt₃BH / tetrahydrofuran / 3 h / 0 °C

8: 100 percent / conc. HCl, H₂ / Pd/C / methanol / 13 h / 2689.2 Torr

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; chloro-trimethyl-silane; lead(II) nitrate; oxalyl dichloride; MoO₅*pyridine*HMPA; hydrogen; lithium perchlorate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo9604245

upstream raw materials:

(S)-1-[(3aS,4R,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-2-methoxymethoxy-ethanol

(2S,3S,4R)-1-Benzyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pyrrolidine-3,4-diol

(S)-1-((3aS,4R,6aR)-5-benzyl-2,2-dimethyltetrahydro-4H-[1,3] dioxolo[4,5-c]pyrrol-4-yl)ethane-1,2-diol

(2S,3S,4R)-N-benzyl-3,4-(isopropylidenedioxy)-2-vinyl-pyrrolidine

Refernces

• 1、 Diez, David,Beneitez, M. Templo,Gil,Moro,Marcos, Isidro S.,Garrido,Basabe,Urones, Julio G.. "Chemistry of epoxysulfones: A new route to polyhydroxylated pyrrolidines". . p. 565 - 568. Retrieved 2007/10/03.
• 2、 Kiess, Frank-Michael,Poggendorf, Philip,Picasso, Sylviane,Jaeger, Volker. "Synthesis of iminopolyols via Henry reaction: A short route to the α-mannosidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol and to amino analogues". . p. 119 - 120. Retrieved 2007/10/03.