1,2:5,6-Bis-O-(1-methylethylidene)-D-mannitol

Base Information

• Chemical Name: 1,2:5,6-Bis-O-(1-methylethylidene)-D-mannitol
• CAS No.: 1707-77-3
• Molecular Formula: C12H22O6
• Molecular Weight: 262.303
• Hs Code.: 29329990
• European Community (EC) Number: 216-954-8
• DSSTox Substance ID: DTXSID201284699
• Nikkaji Number: J80.294H
• Mol file: 1707-77-3.mol

Synonyms:Mannitol,1,2:5,6-di-O-isopropylidene-, D- (8CI);1,2:5,6-Di-O-isopropylidene-D-mannitol;1,2:5,6-Diisopropylidene-D-mannitol;D-(+)-1,2:5,6-Di-O-isopropylidenemannitol;D-Mannitol 1,2:5,6-bis-acetonide;

Chemical Property of 1,2:5,6-Bis-O-(1-methylethylidene)-D-mannitol

Chemical Property:

• Appearance/Colour: odorless White crystalline.
• Vapor Pressure: 2.08E-07mmHg at 25°C
• Melting Point: 120-122 °C(lit.)
• Refractive Index: 6.5 ° (C=8, CHCl3)
• Boiling Point: 382 °C at 760 mmHg
• PKA: 12.98±0.20(Predicted)
• Flash Point: 184.8 °C
• PSA: 77.38000
• Density: 1.175 g/cm³
• LogP: 0.01120
• Storage Temp.: 2-8°C
• Solubility.: methanol: 100 mg/mL, clear, colorless
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 262.14163842
• Heavy Atom Count: 18
• Complexity: 273

Purity/Quality:

98%, ^*data from raw suppliers

1,2:5,6-Di-O-isopropylidene-D-mannitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(OCC(O1)C(C(C2COC(O2)(C)C)O)O)C
• Isomeric SMILES: CC1(OC[C@@H](O1)[C@H]([C@@H]([C@H]2COC(O2)(C)C)O)O)C
• Uses: Nebivolol intermediate.

Technology Process of 1,2:5,6-Bis-O-(1-methylethylidene)-D-mannitol

There total 31 articles about 1,2:5,6-Bis-O-(1-methylethylidene)-D-mannitol 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: 98.0%

3,4-di-O-acetyl-1,2:5,6-di-O-isopropylidene-D-mannitol (76880-55-2) → 1,2:5,6-di-O-isopropylidene-D-mannitol (1707-77-3)

Guidance literature:

With potassium cyanide; In methanol; Ambient temperature;

DOI:10.1016/0008-6215(91)89029-F

Reference yield: 96.0%

mannitol (69-65-8) + 2,2-dimethoxy-propane (77-76-9) → 1,2:5,6-di-O-isopropylidene-D-mannitol (1707-77-3)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.3390/ph12030108

Reference yield: 95.0%

mannitol (69-65-8) + acetone (67-64-1) → 1,2:5,6-di-O-isopropylidene-D-mannitol (1707-77-3)

Guidance literature:

With zinc(II) chloride; at 23 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.10.115

upstream raw materials:

mannitol

O⁴-benzoyl-O¹,O²;O⁵,O⁶-diisopropylidene-D-arabino-[3]hexulose

2-Methoxypropene

1,2:3,6:4,5-tri-O-isopropylidene-D-mannitol

Downstream raw materials:

(R)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid

(1R,2S)-2-(tert-Butyl-diphenyl-silanyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

1,6-dideoxy-1,6-imino-D-mannitol

(3R,4R,5R,6R)-N-benzyl-4,5-di-O-allyl-3,4,5,6-tetrahydroxyazepane

Refernces

• 1、 Chittenden, Gordon J. F.. "ISOPROPYLIDENATION OF D-MANNITOL UNDER NEUTRAL CONDITIONS". . p. 219 - 226. Retrieved 1980.
• 2、 Chittenden, Gordon J. F.. "An improved, simplified synthesis of 1,2:5,6-di-O-isopropylidene-D-mannitol". . p. 350 - 352. Retrieved 1980.
• 3、 Wang, Yan,Dai, Wei-Min. "Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone". . p. 187 - 196. Retrieved 2010.
• 4、 Baer. "-". . p. 338. Retrieved 1945.
• 5、 Corti, Marco,Leusciatti, Marco,Moiola, Mattia,Mella, Mariella,Quadrelli, Paolo. "Nitrosocarbonyl Carbohydrate Derivatives: Hetero Diels-Alder and Ene Reaction Products for Useful Organic Synthesis". . p. 574 - 586. Retrieved 2020/10/06.
• 6、 Ribeiro, Talita A.,Machado-Ferreira, Erik,Guimar?es, Lohaine F.,Cavaleiro, Jéssica,Britto, Alan Messala A.,Redua, Nátaly,de Souza, Lucas Miguel Pereira,Pimentel, André S.,Picciani, Paulo H.S.,Oliveira, Osvaldo N.,Barreto, Cléber Bonfim,Soares, Carlos Augusto G.. "Novel cytotoxic amphiphilic nitro-compounds derived from a synthetic route for paraconic acids". . . Retrieved 2021/06/21.