63167-67-9

Basic information

• Product Name: Methyl 4,6-O-Isopropylidene-a-D-mannopyranoside
• Synonyms: Methyl 4,6-O-(1-Methylethylidene)-a-D-mannopyranoside;Methyl 4,6-O-(1-Methylethylidene)-α-D-mannopyranoside;Methyl 4,6-O-Isopropylidene-α-D-mannopyranoside
• CAS NO: 63167-67-9
• Molecular Formula: C₁₀H₁₈O₆
• Molecular Weight: 234.25
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 63167-67-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 85-86°C
• Boiling Point: 369.218°C at 760 mmHg
• Flash Point: 177.097°C
• Appearance: /
• Density: 1.301g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.514
• Solubility: Methanol
• CAS DataBase Reference: Methyl 4,6-O-Isopropylidene-a-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4,6-O-Isopropylidene-a-D-mannopyranoside(63167-67-9)
• EPA Substance Registry System: Methyl 4,6-O-Isopropylidene-a-D-mannopyranoside(63167-67-9)

Safety Data

• Hazardous Substances Data: 63167-67-9(Hazardous Substances Data)

Usage

Description

Methyl 4,6-O-Isopropylidene-a-D-mannopyranoside is a white crystalline solid that serves as a key intermediate in the synthesis of various a-mannosides. It is a derivative of a-D-mannopyranoside, a monosaccharide, with an isopropylidene group protecting the 4 and 6 hydroxyl groups. This protection allows for selective reactions at other positions on the molecule, making it a valuable compound in organic chemistry and carbohydrate chemistry.

Uses

1. Used in the Synthesis of a-Mannosides:
Methyl 4,6-O-Isopropylidene-a-D-mannopyranoside is used as a synthetic intermediate for the preparation of a-mannosides. Its protected structure allows for selective functionalization at other positions, which is crucial in the synthesis of complex carbohydrate structures.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 4,6-O-Isopropylidene-a-D-mannopyranoside is used as a building block for the development of drugs targeting specific receptors or enzymes. Its ability to form a-mannosides can be exploited in the design of glycoconjugates, which have potential applications in the treatment of various diseases.
3. Used in Chemical Research:
Methyl 4,6-O-Isopropylidene-a-D-mannopyranoside is also utilized in academic and industrial research settings for the study of carbohydrate chemistry, glycobiology, and the development of new synthetic methods. Its unique structure makes it an attractive candidate for exploring novel reactions and understanding the role of carbohydrates in biological systems.
4. Used in Material Science:
In material science, Methyl 4,6-O-Isopropylidene-a-D-mannopyranoside can be employed in the development of new materials with specific properties, such as improved biocompatibility or enhanced recognition capabilities. Its ability to form a-mannosides can be used to create carbohydrate-based materials for various applications, including drug delivery and sensing.

InChI:InChI=1/C10H18O6/c1-10(2)14-4-5-8(16-10)6(11)7(12)9(13-3)15-5/h5-9,11-12H,4H2,1-3H3/t5?,6-,7-,8-,9+/m1/s1

Upstream product

• 116-11-0 2-Methoxypropene 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 77-76-9 2,2-dimethoxy-propane 
• 67-56-1 methanol 
• 51450-36-3 4,6-O-isopropylidene-D-glucal 

Downstream Products

• 82186-14-9 (4aR,6S,7S,8R,8aR)-8-[Bis-(4-methoxy-phenyl)-methoxy]-6-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 82186-11-6 methyl 2-O-[di(4-chlorophenyl)methyl]-4,6-O-isopropylidene-α-D-mannopyranoside 
• 82186-12-7 methyl 3-O-[di(4-chlorophenyl)methyl]-4,6-O-isopropylidene-α-D-mannopyranoside, 
• 82186-09-2 methyl 4,6-O-isopropylidene-2-O-[di(4-methylphenyl)methyl]-α-D-mannopyranoside 
• 82186-10-5 methyl 4,6-O-isopropylidene-3-O-[di(4-methylphenyl)methyl]-α-D-mannopyranoside 
• 74948-73-5 methyl 2,3-O-carbonyl-4,6-O-isopropylidene-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 13035-60-4 methyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside 
• 78462-60-9 Toluene-4-sulfonic acid (4aR,6S,7S,8R,8aR)-7-hydroxy-6-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 82186-07-0 methyl 2-O-diphenylmethyl-4,6-O-isopropylidene-α-D-mannopyranoside 
• 82186-08-1 (4aR,6S,7S,8R,8aR)-8-Benzhydryloxy-6-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 539824-98-1 methyl 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-isopropylidene-α-D-mannopyranosyl-(1->3)-4,6-O-isopropylidene-α-D-mannopyranoside 
• 539824-99-2 methyl 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2-O-acetyl-4,6-O-isopropylidene-α-D-mannopyranosyl-(1->3)-2-O-acetyl-4,6-O-isopropylidene-α-D-mannopyranoside 
• 78462-69-8 (2S,4R,5S,6S)-4-Benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-carbaldehyde 

Relevant articles and documents

Sequential directed epoxydation-acidolysis from glycals with MCPBA. A flexible approach to protected glycosyl donors

4,6-Di-O-protected glucal and allal derivatives react with MCPBA to afford manno- and allo-1-O-m-chlorobenzoate derivatives, respectively, as a result of a syn epoxidation directed by the allylic hydroxyl group, and consecutive ring-opening by m-ClBzOH. When glucal and allal derivatives are fully protected, initial epoxidation proceeds mainly anti to the allylic group to give, after ring-opening, the corresponding pyranosyl chlorobenzoates. Stereoselectivity in the reaction of fully protected galactal derivatives was complete, although only a moderate increase in the syn epoxidation product was observed in 4,6- and 3,4-di-O-protected derivatives. 1-O-m-Chlorobenzoate 18 was selectively protected and activated as donor in the synthesis of disaccharide 21.

Stereocontrolled Total Synthesis of (-)-Maytansinol

Chiral maytansinol (1) was synthesized stereoselectively from D-mannose.Asymmetric centers of 1 were induced intramolecularly from an asymmetric carbon corresponding to C-7 via the common key intermediate 3 for maytansinoids.Key points are (i) the usage o

SYNTHETIC STUDIES TOWARD MAYTANSINOIDS. PREPARATION OF THE OPTICALLY ACTIVE INTERMEDIATES FROM D-MANNOSE

Optically active intermediates (15 and 23) for maytansine were synthesized from D-mannose via heteroconjugate addition of methyllithium as a crucial step.