6,7-Dihydroxyswainsonine

Base Information

• Chemical Name: 6,7-Dihydroxyswainsonine
• CAS No.: 144367-16-8
• Molecular Formula: C₈H₁₅NO₅
• Molecular Weight: 205.211
• DSSTox Substance ID: DTXSID30446432
• Nikkaji Number: J562.916K
• Wikidata: Q82265066
• Mol file: 144367-16-8.mol

Synonyms:6,7-DIHYDROXYSWAINSONINE;144367-16-8;(1S,2R,6R,7R,8S,8aS)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,6,7,8-pentol;DTXSID30446432;AKOS030241521;(1S,8abeta)-Octahydroindolizine-1alpha,2alpha,6beta,7beta,8beta-pentol

Chemical Property of 6,7-Dihydroxyswainsonine

Chemical Property:

• Melting Point: 175°C dec.
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol, Water
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 205.09502258
• Heavy Atom Count: 14
• Complexity: 226

Purity/Quality:

95% ^*data from raw suppliers

6,7-Dihydroxyswainsonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(C2N1CC(C(C2O)O)O)O)O
• Isomeric SMILES: C1[C@H]([C@H]([C@@H]2N1C[C@H]([C@H]([C@H]2O)O)O)O)O
• Uses: Swainsonine analogue; inhibits a-mannosidase with 20-to 100-fold less activity 6,7-Dihydroxyswainsonine is an analog of Swainsonine (CAT# S885000), which is a plant alkaloid and inhibitor of α-?mannosidase, a target for drug development in anti-?tumor therapies. 6,7-Dihydroxyswainsonine inhibits α-?mannosidase with 20-to 100-fold less activity.

Technology Process of 6,7-Dihydroxyswainsonine

There total 8 articles about 6,7-Dihydroxyswainsonine 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: 82.0%

1,5-dideoxy-1,5-imino-D-erythro-L-allo-octitol (144367-15-7) → (-)-(1S,2R,6R,7R,8S,8aS)-1,2,6,7,8-Pentahydroxyindolizidine (144367-16-8)

Guidance literature:

With pyridine; tetrachloromethane; triethylamine; triphenylphosphine; at 20 ℃; for 15h;

DOI:10.1016/S0040-4039(00)61233-9

Reference yield:

(1R,4R,5S,6S,7S)-4-exo-<(1'S,2'R)-1'-Hydroxy-2',3'-(isopropylidenedioxy)propyl>-6-exo,7-exo-(isopropylidenedioxy)-2,8-dioxabicyclo<3.2.1>octan-3-one (125284-31-3,129830-02-0) → (-)-(1S,2R,6R,7R,8S,8aS)-1,2,6,7,8-Pentahydroxyindolizidine (144367-16-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 76 percent / CsF / dimethylsulfoxide / 20 °C

2: 2,6-lutidine / CH₂Cl₂ / 0 °C

3: H₂ / Pd-C / ethyl acetate / 20 °C

4: 1) N₃PO(OPh)2, NEt₃ / 1) toluene, 2) 100 deg C, 15h

5: Bu₄NF / tetrahydrofuran / 0 to 20 deg C

6: H₂ / 10percent Pd-C / ethyl acetate / 24 h / 20 °C

7: 96 percent / TFA / H₂O / 5 h / 20 °C

8: 82 percent / PPh₃, CCl₄, pyridine, NEt₃ / 15 h / 20 °C

With pyridine; 2,6-dimethylpyridine; tetrachloromethane; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; hydrogen; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/S0040-4039(00)61233-9

Reference yield:

[(1S,2S)-1-[(S)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-((4S,5S)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-ethyl]-carbamic acid benzyl ester → (-)-(1S,2R,6R,7R,8S,8aS)-1,2,6,7,8-Pentahydroxyindolizidine (144367-16-8)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 10percent Pd-C / ethyl acetate / 24 h / 20 °C

2: 96 percent / TFA / H₂O / 5 h / 20 °C

3: 82 percent / PPh₃, CCl₄, pyridine, NEt₃ / 15 h / 20 °C

With pyridine; tetrachloromethane; hydrogen; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In water; ethyl acetate;

DOI:10.1016/S0040-4039(00)61233-9

upstream raw materials:

1,5-dideoxy-1,5-imino-D-erythro-L-allo-octitol

(1R,4R,5S,6S,7S)-4-exo-<(1'S,2'R)-1'-Hydroxy-2',3'-(isopropylidenedioxy)propyl>-6-exo,7-exo-(isopropylidenedioxy)-2,8-dioxabicyclo<3.2.1>octan-3-one

(-)-1,5-Dideoxy-1,5-imino-2,3:7,8-di-O-isopropylidene-D-erythro-L-allo-octitol

(+)-tert-Butyldimethylsilyl 5-C-(benzyloxycarbonyl)-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3:7,8-di-O-isopropylidene-α-D-erythro-L-allo-octofuranoside

Refernces

• 1、 Chen,Vogen. "Total syntheses of 1,5-dideoxy-1,5-imino-D-erythro-L-allo-octitol and (1S,2R,6R,7R,8S,8aS)-pentahydroxyindolizidine". . p. 4917 - 4920. Retrieved 2007/10/02.