38145-93-6

Basic information

• Product Name: (R)-1-[(4R,4'R)-2,2,2',2'-Tetramethyl-4α,4'β-bi[1,3-dioxolane]-5β-yl]ethane-1,2-diol
• Synonyms: (R)-1-[(4R,4'R)-2,2,2',2'-Tetramethyl-4α,4'β-bi[1,3-dioxolane]-5β-yl]ethane-1,2-diol;1-O,2-O:3-O,4-O-Bis(1-methylethylidene)-D-mannitol
• CAS NO: 38145-93-6
• Molecular Formula: C₁₂H₂₂O₆
• Molecular Weight: 0
• Mol File: 38145-93-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-1-[(4R,4'R)-2,2,2',2'-Tetramethyl-4α,4'β-bi[1,3-dioxolane]-5β-yl]ethane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-[(4R,4'R)-2,2,2',2'-Tetramethyl-4α,4'β-bi[1,3-dioxolane]-5β-yl]ethane-1,2-diol(38145-93-6)
• EPA Substance Registry System: (R)-1-[(4R,4'R)-2,2,2',2'-Tetramethyl-4α,4'β-bi[1,3-dioxolane]-5β-yl]ethane-1,2-diol(38145-93-6)

Safety Data

• Hazardous Substances Data: 38145-93-6(Hazardous Substances Data)

Usage

Description

(R)-1-[(4R,4'R)-2,2,2',2'-Tetramethyl-4α,4'β-bi[1,3-dioxolane]-5β-yl]ethane-1,2-diol is a chiral compound characterized by its central ethane-1,2-diol core and two 2,2,2',2'-tetramethyl-4α,4'β-bi[1,3-dioxolane] groups. With a molecular formula of C18H34O6 and a molecular weight of 346.46 g/mol, this compound is recognized for its unique structure and potential applications in various fields, including drug development and material science. Its stereochemistry and functional groups make it a valuable asset in the synthesis of complex molecules and the exploration of biological activities.

Uses

Used in Pharmaceutical Research:
(R)-1-[(4R,4'R)-2,2,2',2'-Tetramethyl-4α,4'β-bi[1,3-dioxolane]-5β-yl]ethane-1,2-diol is used as a building block for the development of new pharmaceutical compounds due to its unique structure and stereochemistry. Its functional groups and molecular configuration allow for the creation of complex molecules with potential therapeutic applications.
Used in Material Science:
In the field of material science, (R)-1-[(4R,4'R)-2,2,2',2'-Tetramethyl-4α,4'β-bi[1,3-dioxolane]-5β-yl]ethane-1,2-diol is utilized as a key component in the synthesis of novel materials with specific properties. Its incorporation into these materials can lead to advancements in areas such as polymer development, nanotechnology, and other material innovations.
Used in Organic Synthesis:
As a chiral compound, (R)-1-[(4R,4'R)-2,2,2',2'-Tetramethyl-4α,4'β-bi[1,3-dioxolane]-5β-yl]ethane-1,2-diol is employed as an essential building block in organic synthesis. Its stereochemistry and functional groups enable the creation of a wide range of complex molecules, which can be further explored for their potential applications in various industries, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Drug Development:
In the pharmaceutical industry, (R)-1-[(4R,4'R)-2,2,2',2'-Tetramethyl-4α,4'β-bi[1,3-dioxolane]-5β-yl]ethane-1,2-diol is used as a starting material for the synthesis of new drugs. Its unique structure and stereochemistry make it a valuable tool in the development of innovative therapeutic agents with improved efficacy and selectivity.
Used in Chiral Catalysts:
The chiral nature of (R)-1-[(4R,4'R)-2,2,2',2'-Tetramethyl-4α,4'β-bi[1,3-dioxolane]-5β-yl]ethane-1,2-diol also makes it a potential candidate for use in chiral catalysis. As a chiral catalyst, it can be employed to control the stereochemistry of various chemical reactions, leading to the production of enantiomerically pure compounds with potential applications in the pharmaceutical, agrochemical, and fragrance industries.

Upstream product

• 69-65-8 mannitol 
• 116-11-0 2-Methoxypropene 
• 77-76-9 2,2-dimethoxy-propane 
• 3969-59-3 mannitol triacetonide 
• 114743-87-2 methyl 3,4;5,6-di-O-isopropylidene-D-gluconate 2-(toluene-p-sulphonate) 
• 3969-59-3 1,2;3,4:5,6-tri-O-isopropylidene-D-glucitol 

Downstream Products

• 910879-97-9 O²-acetyl-O³,O⁴;O⁵,O⁶-diisopropylidene-O¹-(toluene-4-sulfonyl)-D-mannitol 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 53636-15-0 (R)-1-(dimethylamino)-2-propanol 
• 23260-97-1 1-Tosyl-D-mannitol 
• 85325-92-4 1,2:3,4-di-O-isopropylidene-6-O-p-toluenesulfonyl-D-mannitol 
• 114743-88-3 C₂₆H₂₈N₂O₁₂ 
• 104527-46-0 3,4:5,6-di-O-isopropylidene-1-O-p-tolylsulfonyl-D-glucitol 
• 203244-60-4 (4R,5R,4'R)-5-{(R)-1,2-Bis-[12-(tetrahydro-pyran-2-yloxy)-dodecyloxy]-ethyl}-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl] 
• 290836-45-2 6-O-benzoyl-1,2:3,4-di-O-isopropylidene-D-mannitol 
• 4239-90-1 (4S,4'R,5R)-2,2,2',2'-tetramethyl-5-vinyl-4,4'-bi(1,3-dioxolane) 
• 838902-32-2 (4R,5R,4'R)-5-((R)-1,2-Bis-benzyloxy-ethyl)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl] 
• 120166-83-8 4,5-di-O-benzyl-2,3-O-isopropylidene-D-arabinose 
• 838902-34-4 arabino-hex-1-[1-13C]enitol 
• 838902-38-8 C₂₂⁽¹³⁾CH₂₈O₅ 

Relevant articles and documents

Zeolite catalyzed selective deprotection of di- and tri-O-isopropylidene sugar acetals

H-Beta zeolite, a microporous solid acid, is demonstrated to be an efficient catalyst for the selective deprotection of cyclic as well as acyclic O-isopropylidene sugar acetals derived from d-glucose, d-xylose, d-mannose, and d-mannitol in aqueous MeOH at room temperature. A notable observation is the conversion of d-mannitol triacetonide into 1,2:3,4-di-O-isopropylidene-d-mannitol (48%) and 3,4-O-isopropylidene-d-mannitol (36%) brought about in 6 h by H-beta zeolite and the non-occurrence of any hydrolysis in the case of H-ZSM-5 catalyzed reaction in 24 h under the same conditions.

ACETONATION OF D-MANNITOL

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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.