[5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

Base Information

• Chemical Name: [5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS No.: 19139-74-3
• Molecular Formula: C11H20 O5
• Molecular Weight: 232.277
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID10398369
• Mol file: 19139-74-3.mol

Synonyms:2,3:4,5-Di-O-isopropylidene-D-arabinitol;[5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol;19139-74-3;SCHEMBL7375244;DTXSID10398369;(2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol;2,3:4,5-DI-O-ISOPROPYLIDENE-D-*ARABINITOL

Chemical Property of [5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

Chemical Property:

• PSA: 57.15000
• LogP: 0.65030
• Storage Temp.: −20°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 232.13107373
• Heavy Atom Count: 16
• Complexity: 263

Purity/Quality:

97% ^*data from raw suppliers

2,3:4,5-Di-O-isopropylidene-D-arabitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)C2C(OC(O2)(C)C)CO)C

Technology Process of [5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

There total 40 articles about [5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol 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%

2,2:4,5-di-O-isopropylidene-D-arabinose (13039-93-5) → 2,3:4,5-di-O-isopropylidene-D-arabinitol (19139-74-3)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;

DOI:10.1021/ja074392m

Reference yield: 85.0%

2,2-dimethoxy-propane (77-76-9) + D-O2,O3-isopropylidene-ribitol (69977-54-4) → ((4S,4’R,5S)-2,2,2’,2’-tetramethyl-[4,4’-bi(1,3-dioxolan)]-5-yl)methanol (3969-86-6,19139-74-3,30737-85-0,84709-27-3,84709-35-3,84709-41-1,127305-49-1,100484-23-9)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 0 - 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2007.07.067

Reference yield: 85.0%

Adonitol (488-81-3) + acetone (67-64-1) → 1,2:3,4-Di-O-isopropylidene-DL-ribitol (3969-86-6,19139-74-3,30737-85-0,84709-27-3,84709-35-3,84709-41-1,100484-23-9,127305-49-1)

Guidance literature:

With toluene-4-sulfonic acid; In various solvent(s); Ambient temperature;

DOI:10.1135/cccc19822786

upstream raw materials:

D-Arabitol

acetone

2,2:4,5-di-O-isopropylidene-D-arabinose

(E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol

Downstream raw materials:

1-deoxy-2,3-o-isopropylidene-1-tosyl-D-arabinitol

D-Arabitol

(4S,4’R,5R)-5-[(benzyloxy)methyl]-2,2,2’,2’-tetramethyl-4,4’-bis[1,3-dioxolane]

1-(Adenin-9-yl)-1-deoxy-D-arabitol

Refernces

• 1、 Raju, Kammari Bal,Kumar, Bejjanki Naveen,Kumar, Bandari Sampath,Nagaiah, Kommu. "Towards stereoselective synthesis of the C(31)-C(39) and C(20)-C(27) fragments of phorboxazole A". . p. 386 - 398. Retrieved 2015/03/18.
• 2、 Richter, Jeremy M.,Whitefield, Brandon W.,Maimone, Thomas J.,Lin, David W.,Castroviejo, M. Pilar,Baran, Phil S.. "Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: Total synthesis of acremoauxin A and oxazinin 3". . p. 12857 - 12869. Retrieved 2008/09/16.