71772-35-5

Usage

Uses

Used in Organic Synthesis:
Methyl 6-Deoxy-3,4-O-isopropylidene-α-D-galactopyranoside is used as a synthetic building block for the creation of more complex organic molecules. Its unique structure allows it to be a valuable component in the synthesis of various compounds, particularly those with biological or pharmaceutical significance.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 6-Deoxy-3,4-O-isopropylidene-α-D-galactopyranoside is used as a key intermediate in the development of new drugs. Its ability to be modified and incorporated into more complex molecules makes it a versatile tool for medicinal chemists working on the design and synthesis of novel therapeutic agents.
Used in Chemical Research:
Methyl 6-Deoxy-3,4-O-isopropylidene-α-D-galactopyranoside is also used as a research tool in the field of chemistry. Its unique properties and reactivity make it an interesting subject for studying various chemical reactions and mechanisms, which can lead to a better understanding of organic chemistry and the development of new synthetic methods.
Used in Material Science:
In material science, Methyl 6-Deoxy-3,4-O-isopropylidene-α-D-galactopyranoside can be used as a component in the development of new materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of materials with unique characteristics, such as improved biocompatibility or enhanced mechanical properties.

InChI:InChI=1/C10H18O5/c1-5-7-8(15-10(2,3)14-7)6(11)9(12-4)13-5/h5-9,11H,1-4H3/t5?,6?,7-,8?,9-/m0/s1

Upstream product

• 67-64-1 acetone 
• 1128-40-1 methyl α-D-fucopyranoside 
• 129172-95-8 methyl 6-deoxy-α/β-D-galactopyranoside 
• 73-34-7 D-Fucose 
• 71732-12-2 (3aR,4S,6S,7R,7aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 3615-37-0 D-Fucose 

Downstream Products

• 901785-62-4 methyl-(O²-benzyl-O³,O⁴-isopropylidene-α-D-fucopyranoside) 
• 74135-23-2 methyl 3,4-O-isopropylidene-2-O-methyl-α-D-fucopyranoside 
• 123076-84-6 methyl 2-O-benzoyl-6-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside 
• 1128-40-1 methyl α-D-fucopyranoside 
• 123076-93-7 methyl 4-O-acetyl-2-O-benzoyl-3,6-dideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-β-D-galactopyranoside 
• 113668-66-9 methyl 4-O-acetyl-2-O-benzoyl-3,6-dideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-α-D-gulopyranoside 
• 123076-90-4 methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone 
• 123076-91-5 methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-β-D-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone 
• 123076-88-0 methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-xylo-hexopyranosid-3-ulose 
• 123076-89-1 methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-β-D-xylo-hexopyranosid-3-ulose 
• 123076-86-8 methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-D-galactopyranoside 
• 123076-87-9 methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-β-D-galactopyranoside 
• 65222-57-3 methyl 2-O-benzoyl-6-deoxy-α-D-galactopyranoside 
• 123163-96-2 methyl 2-O-benzoyl-6-deoxy-β-D-galactopyranoside 

Relevant academic research and scientific papers

A convenient synthesis of furanose-free D-fucose per-O-acetates and a precursor for anthrose

Methyl 3,4-O-isopropylidene-α- or β-D-galactopyranoside was iodinated with triiodoimidazole in the presence of triphenylphosphane and the corresponding 6-deoxy-6-iodo derivatives 5 or 6, respectively, were converted to furanose-free 1,2,3,4-tetra-O-acetyl-α,β-D-fucopyranose. A key intermediate for chemical synthesis of anthrose, a constituent of the tetrasaccharide of major glycoprotein of Bacillus anthracis exosporium, 1-O-acetyl-4-azido-2-O-benzoyl-3-O-benzyl-4,6-dideoxy-α, β-D-glucopyranose, was synthesized from 5 or 6 in 7 steps. The latter was readily converted into the corresponding 1-O-trichloroacetimidate. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Studies of the Mechanistic Diversity of Sodium Cyanoborohydride Reduction of Tosylhydrazones

Reduction of tosylhydrazone derivatives of ketones and aldehydes with sodium cyanoborohydride in acidic medium is a mild, albeit versatile, deoxygenation reaction.The reaction mechanism has been proposed to proceed via either a direct hydride attack route or a tautomerization-then-reduction route.By using a mild reduction procedure (NaBH3CN, THF-MeOH, 0 deg C), it has been possible to stop the deoxygenation halfway and isolate the nascent tosylhydrazine product.Characterization of the resulting hydrazine to define the origin of the hydrogen being delivered to theformer carbonyl carbon has allowed us to unambiguously distinguish between these two possible mechanisms.Studies of reduction of tosylhydrazones derived from conjugated and saturated ketones confirmed earlier speculation that these reductions occur through a direct hydride attack mechanism.The reduction of para-substituted methyl phenyl ketone tosylhydrazones revealed a competition between these two mechanisms.Substrates bearing electron-donating substituents prefer to direct hydride attack pathway, while those with electron-withdrawing substituents favor an initial tautomerization prior to reduction.Sugar and hydroxyl ketone tosylhydrazones are also reduced by competing mechanisms.The mechanistic diversity in those cases may be attributed to the inductive effects compelled by the α substituents and the conformational constraints imposed by the ring structure.The mechanistic insights gained from these studies indicate that the direct hydride attack mechanism is the main reaction pathway due to the propensity of NaBH3CN to selectively attack the iminium ion.The tautomerization-then-reduction mechanism prevails only when the tautomerization of hydrazon to azohydrazine is facilitated.