4306-35-8

Basic information

• Product Name: 1,2-O-ISOPROPYLIDENE-D-MANNITOL
• Synonyms: 1,2-O-ISOPROPYLIDENE-D-MANNITOL
• CAS NO: 4306-35-8
• Molecular Formula: C₉H₁₈O₆
• Molecular Weight: 222.24
• Product Categories: Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 4306-35-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 158-161 °C(lit.)
• Boiling Point: 458.7°Cat760mmHg
• Flash Point: 231.2°C
• Appearance: /
• Density: 1.318g/cm³
• Vapor Pressure: 2.41E-10mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: 1,2-O-ISOPROPYLIDENE-D-MANNITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-ISOPROPYLIDENE-D-MANNITOL(4306-35-8)
• EPA Substance Registry System: 1,2-O-ISOPROPYLIDENE-D-MANNITOL(4306-35-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 4306-35-8(Hazardous Substances Data)

Usage

General Description

1,2-O-ISOPROPYLIDENE-D-MANNITOL is a chemical compound commonly used as a protecting group for hydroxyl groups in organic synthesis. It is a derivative of mannitol, a naturally occurring sugar alcohol found in plants and fungi. The isopropylidene group serves as a temporary shield for the hydroxyl group, allowing for selective reactions to occur without interference from other functional groups. 1,2-O-ISOPROPYLIDENE-D-MANNITOL is widely used in organic chemistry for the synthesis of various compounds and as a building block in the production of pharmaceuticals and other fine chemicals. Additionally, 1,2-O-ISOPROPYLIDENE-D-MANNITOL is considered to be relatively non-toxic and environmentally friendly, making it a popular choice for chemical reactions in both academic and industrial settings.

InChI:InChI=1/C9H18O6/c1-9(2)14-4-6(15-9)8(13)7(12)5(11)3-10/h5-8,10-13H,3-4H2,1-2H3

Upstream product

• 69-65-8 mannitol 
• 116-11-0 2-Methoxypropene 
• 91667-55-9 1,2:3,6:4,5-tri-O-isopropylidene-D-mannitol 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 
• 71696-36-1 3,4-di-O-acetyl-1,2:5,6-di-O-isopropylidene-D-glucitol 
• 50-70-4 D-glucitol 
• 81541-12-0 1,3:2,4-di-O-(4-methylbenzylidene)-D-sorbitol 

Downstream Products

• 33818-33-6 O³,O⁴,O⁵,O⁶-tetrabenzoyl-O¹,O²-isopropylidene-D-glucitol 
• 497-09-6 (S)-glyceraldehyde 
• 33818-33-6 O¹,O²,O³,O⁴-tetrabenzoyl-O⁵,O⁶-isopropylidene-D-mannitol 
• 58794-71-1 C₃₆H₄₂O₆ 
• 58846-24-5 3,4,5,6-tetra-O-benzyl-D-sorbitol 
• 35775-37-2 O¹,O²-isopropylidene-O³,O⁴;O⁵,O⁶-bis-phenylboranediyl-D-glucitol 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 
• 53735-98-1 1,2:5,6-di-O-isopropylidene-D-glucitol 
• 73707-74-1 1,2:4,6-di-O-isopropylidene-D-glucitol 
• 3969-61-7 2,3:5,6-di-O-isopropylidene-D-glucitol 
• 73707-73-0 1,2;3,5:4,6-tri-O-isopropylidene-D-glucitol 
• 3969-59-3 1,2;3,4:5,6-tri-O-isopropylidene-D-glucitol 
• 53735-98-1 (1S,2S)-1,2-bis[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol 
• 4239-88-7 O¹,O²;O³,O⁴;O⁵,O⁶-triisopropylidene-D-glucitol 

Relevant articles and documents

Functional importance of the sugar moiety of jasmonic acid glucoside for bioactivity and target affinity

12-O-β-d-Glucopyranosyljasmonic acid (JAG, 1) induces nyctinastic leaf-folding of Samanea saman. The SAR studies of 1 revealed the unique role of its glycone moiety. Biological activity and the target affinity of 1 were affected by the stereochemistry of the glycone moiety. JAG belongs to a unique class of ligands in which the structure of the glycone moiety is involved in the molecular recognition by the target protein. This journal is

THE SYNTHESIS OF 1,2:5,6-DI-O-ISOPROPYLIDENE-D-MANNITOL: A COMPARATIVE STUDY

Three different methods of acetonation of D-mannitol using (a) acetone and zinc chloride, (b) 2,2-dimethoxypropane, 1,2-dimethoxyethane, and tin(II)chloride, and (c) 2-methoxypropane, N,N-dimethylformamide, and p-toluenesulfonic acid were studied in detail and compared, using gas-liquid chromatographic techniques.In each reaction, isomeric diacetals are formed, but method a gives the 1,2:5,6-diacetal in the highest yield (63percent).Methods b and c give a more complex mixture of acetals than proposed in the literature, and both methods are less economical than a.A new 1,2:3,6:4,5-tri-O-isopropylidene-D-mannitol could be separated, and its graded hydrolysis was compared to that of the 1,2:3,4:5,6-triacetal.

ISOPROPYLIDENATION OF D-MANNITOL UNDER NEUTRAL CONDITIONS

Isopropylidenation of D-mannitol (2) under neutral conditions, by treatment with 2,2-dimethoxypropane in 1,2-dimethoxyethane, is described. 1,2:5,6-Di-O-isopropylidene-D-mannitol is the main equilibrium product, which does not undergo further substitution under the conditions used. 1,2:3,4:5,6-Tri-O-isopropylidene-D-mannitol, the other major product, was shown to be derived mainly from initial 3,4-substitution of 2.The presence of a difunctional ether, of suitable geometry, is a necessary requirement for the reaction.Some mechanistic aspects of the reaction are discussed.