1,2-Isopropylidene Swainsonine

Base Information

• Chemical Name: 1,2-Isopropylidene Swainsonine
• CAS No.: 85624-09-5
• Molecular Formula: C11H19NO3
• Molecular Weight: 213.277
• DSSTox Substance ID: DTXSID20431938
• Nikkaji Number: J2.494.966D
• Mol file: 85624-09-5.mol

Synonyms:1,2-Isopropylidene Swainsonine;85624-09-5;(3aR,9R,9aR,9bS)-2,2-dimethyl-3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-ol;Swainsonine Acetonide;DTXSID20431938;HEVZREBCOASZGR-ZYUZMQFOSA-N;(1S,8abeta)-1alpha,2alpha-(Isopropylidenedioxy)octahydroindolizine-8beta-ol;(3AR,9R,9AR,9BS)-2,2-DIMETHYL-OCTAHYDRO-[1,3]DIOXOLO[4,5-A]INDOLIZIN-9-OL

Chemical Property of 1,2-Isopropylidene Swainsonine

Chemical Property:

• PSA: 41.93000
• LogP: 0.28330
• Solubility.: Chloroform
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 213.13649347
• Heavy Atom Count: 15
• Complexity: 269

Purity/Quality:

99% ^*data from raw suppliers

1,2-Isopropylidene Swainsonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2CN3CCCC(C3C2O1)O)C
• Isomeric SMILES: CC1(O[C@@H]2CN3CCC[C@H]([C@@H]3[C@@H]2O1)O)C
• Uses: 1,2-Isopropylidene Swainsonine is used in the synthesis of Swainsonine (S885000) which is a plant alkaloid derived from Swainsona canescens (a leguminous plant). It is a reversible, active-site directed inhibitor of a-mannosidase at concentrations of 5-10mM. At acid pH, swainsonine resembles an intermediate in the hydrolysis of mannosidases.

Technology Process of 1,2-Isopropylidene Swainsonine

There total 205 articles about 1,2-Isopropylidene Swainsonine 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%

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine (154815-12-0) → (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol (85624-09-5)

Guidance literature:

With hydrogen; palladium dichloride; In methanol; at 20 ℃; for 0.5h;

DOI:10.1021/jo025977w

Reference yield: 94.0%

(1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one (107080-62-6,127420-72-8,98362-03-9) → (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol (85624-09-5)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; 0 deg C, 30 min, room temperature, 2 h;

DOI:10.1021/jo961101b

Reference yield: 90.0%

(1(S),2(R),8(S),8a(S))-8-Hydroxy-1,2-(isopropylidenedioxy)octahydro-5-indolizidinone (152185-81-4) → (1S,2R,8S,8aS)-8-hydroxy-1,2-O-iso-propylideneoctahydro-1,2,8-indolizidine triol (85624-09-5,102208-65-1,105452-57-1,116497-18-8)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/j.tet.2012.06.006

upstream raw materials:

(3aR,9bS)-2,2-Dimethyl-3a,4,6,7,8,9b-hexahydro-[1,3]dioxolo[4,5-a]indolizine

(1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane

(-)-(7S,8R)-7,8-O-isopropylidenedioxy-2-oxo-1-azabicyclo<4.3.0>non-5-ene

(1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one

Downstream raw materials:

swainsonine

Benzoic acid (3aR,9R,9aR,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester

Benzoic acid (3aR,8aS,9S,9aR)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-f]indolizin-9-yl ester

(1S,2R,8S,8aS)-octahydro-1,2,8-indolizidinetriol