4306-35-8

Usage

Uses

Used in Organic Chemistry:
1,2-O-ISOPROPYLIDENE-D-MANNITOL is used as a protecting group for hydroxyl groups, allowing for selective reactions to occur without interference from other functional groups. This application is crucial for the synthesis of various compounds in organic chemistry.
Used in Pharmaceutical Production:
1,2-O-ISOPROPYLIDENE-D-MANNITOL serves as a building block in the production of pharmaceuticals, contributing to the development of new drugs and medicines.
Used in Fine Chemicals Industry:
1,2-O-ISOPROPYLIDENE-D-MANNITOL is also utilized as a key component in the synthesis of fine chemicals, which are high-purity chemicals used in various applications, including research, diagnostics, and specialty manufacturing.
Used in Environmentally Friendly Chemical Reactions:
Due to its relatively non-toxic and environmentally friendly properties, 1,2-O-ISOPROPYLIDENE-D-MANNITOL is favored for chemical reactions that prioritize safety and sustainability 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 
• 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 (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 
• 74923-97-0 (R)-2,2-dimethyl-4-(cyanomethyl)-1,3-dioxolane 
• 23735-43-5 (S)-1-O-tosyl-2,3-O-isopropylideneglycerol 
• 33818-33-6 O¹,O²,O³,O⁴-tetrabenzoyl-O⁵,O⁶-isopropylidene-D-mannitol 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 131425-08-6 1,2,3,4-tetra-O-p-chlorobenzoyl-D-mannitol 
• 117858-83-0 N-benzyl-1,4-dideoxy-2,3:5,6-di-O-isopropylidene-1,4-imino-D-allitol 

Relevant academic research and scientific papers

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.

REINVESTIGATION OF THE ACETALATION OF D-GLUCITOL WITH ACETONE-ZINC CHLORIDE

The acetonation of D-glucitol in the presence of zinc chloride has been studied in detail by gas-liquid chromatographic techniques.From among the 12 different peaks, those belonging to the 1,2:3,4:5,6-tri-, 1,2:3,5:4,6-tri-, 3,4:5,6-di-, 2,3:5,6-di-, 1,2:3,4-di-, 1,2:5,6-di-, 1,2:4,6-di-, 1,2-mono-, 2,3-mono-, 3,4-mono-, and 5,6-mono-acetals could be identified.The course of the reaction was also studied by g.l.c.From the time dependent ratio of the different acetals, it could be concluded that the reaction is kinetically controlled at the beginning, when terminal acetals are mainly formed.In the thermodinamically controlled equilibrium, reached after 5 days, the 1,2:3,4:5,6-tri- and the 2,3:5,6-di-acetal are present in almost equal proportions.The structure of the (new) 1,2:3,5:4,6-triacetal was established by mass-spectrometric and 13C-n.m.r. investigation.

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.