111830-53-6

Basic information

• Product Name: 3,6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL
• Synonyms: 3,6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL
• CAS NO: 111830-53-6
• Molecular Formula: C₁₈H₃₈O₄Si₂
• Molecular Weight: 408.68
• Product Categories: Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 111830-53-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 43-45 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• CAS DataBase Reference: 3,6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL(111830-53-6)
• EPA Substance Registry System: 3,6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-GLUCAL(111830-53-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 111830-53-6(Hazardous Substances Data)

Upstream product

• 2873-29-2 D-glucal triacetate 
• 83-87-4 D-glucose pentaacetate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 13265-84-4 D-glucal 
• 143422-89-3 (2-methylallyl)tertiobutyl-dimethylsilane 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 132891-79-3 4-O-benzyl-1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose 
• 111830-58-1 4-O-benzyl-1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose 
• 13265-84-4 D-glucal 
• 913258-74-9 3,6-O-di-tert-butyldimethylsilyl-4-O-p-methoxybenzyl-D-glucal 
• 916154-05-7 (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran 
• 916154-04-6 ((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol 
• 916153-96-3 (4R,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-6-vinyltetrahydropyran-2-one 
• 916154-06-8 methyl (3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-4-(p-methoxybenzyloxy)hept-6-enoate 
• 916153-95-2 (S)-hept-6-en-2-yl (3R,5S)-3-benzoyloxy-5-benzyloxy-4-oxo-hept-6-enoate 
• 916154-12-6 (S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate 
• 916154-07-9 methyl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate 
• 916154-09-1 (S)-hept-6-en-2-yl (3R,4S,5S)-5-benzyloxy-3-hydroxy-4-(p-methoxybenzyloxy)hept-6-enoate 
• 916154-08-0 (S)-hept-6-en-2-yl (3R,4R,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)hept-6-enoate 
• 916154-11-5 (S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-(p-methoxybenzyloxy)hept-6-enoate 

Relevant articles and documents

DIRECT 3,6-DI-O-PROTECTION OF GLUCAL AND GALACTAL

tert.-Butyldimethylsilyl chloride is a useful reagent for direct 3,6-di-O-protection of D-glucal and D-galactal.The unprotected 4-hydroxy group is still accessible to other protective groups providing after selective 3,6-O-desilylation 4-O-protected deriv

2-nitroglycal and efficient synthesis method thereof

The invention discloses an efficient synthesis method of 2-nitroglycal, and belongs to the technical field of synthesis of sugar. The structure of the 2-nitroglycal is shown in the specification. Secondly, the invention also provides a preparation method of the 2-nitro saccharide alkene, and the preparation method provided by the invention can be used for efficiently preparing the 2-nitroglycal through one-step synthesis.

A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.