4933-77-1

Basic information

• Product Name: 1,2:3,4-Di-O-isopropylidene-α-D-galacto-hexadialdo-1,5-pyranose
• Synonyms: 1,2:3,4-Di-O-isopropylidene-α-D-galacto-hexadialdo-1,5-pyranose;(3aR,5S,5aR,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-carbaldehyde
• CAS NO: 4933-77-1
• Molecular Formula: C₁₂H₁₈O₆
• Molecular Weight: 258.27
• Mol File: 4933-77-1.mol
• Article Data: 51

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,2:3,4-Di-O-isopropylidene-α-D-galacto-hexadialdo-1,5-pyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:3,4-Di-O-isopropylidene-α-D-galacto-hexadialdo-1,5-pyranose(4933-77-1)
• EPA Substance Registry System: 1,2:3,4-Di-O-isopropylidene-α-D-galacto-hexadialdo-1,5-pyranose(4933-77-1)

Safety Data

• Hazardous Substances Data: 4933-77-1(Hazardous Substances Data)

Usage

General Description

1,2:3,4-Di-O-isopropylidene-α-D-galacto-hexadialdo-1,5-pyranose is a chemical compound used in organic synthesis and carbohydrate chemistry. It is a derivative of D-galactose and is commonly used as a protecting group for the hydroxyl groups in carbohydrates. The compound is a white to off-white powder with a molecular formula of C14H24O6 and a molecular weight of 288.34 g/mol. It has a melting point of around 140-143°C and is soluble in various organic solvents such as acetone and ethyl acetate. 1,2:3,4-Di-O-isopropylidene-α-D-galacto-hexadialdo-1,5-pyranose is important in the development of new drugs, as well as the synthesis of complex natural products and pharmaceuticals.

Upstream product

• 4026-28-2 1,2:3,4-di-O-isopropylidene-6-iodo-D-galactopyranose 
• 10257-28-0 D-Galactose 
• 67-68-5 dimethyl sulfoxide 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 35017-07-3 6-deoxy-6-(N-hydroxyimino)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 292638-85-8 acrylic acid methyl ester 
• 59-23-4 D-Galactose 
• 118893-77-9 (3aR,5S,6R,7S,7aR)-5-Furan-2-yl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 
• 25253-46-7 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carboxylic acid 
• 99166-39-9 (3aR,5S,5aR,8aS,8bR)-5-Furan-2-yl-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 118920-26-6 C₂₃H₂₀O₈ 
• 118893-76-8 C₂₆H₂₄O₈ 
• 1010075-67-8 C₁₅H₂₄O₅S₂ 
• 3646-73-9 α-D-galactopyranose 

Downstream Products

• 91860-98-9 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-oct-7-enopyranose 
• 91860-99-0 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-β-L-glycero-D-galacto-oct-7-enopyranose 
• 191997-37-2 (Z)-N-benzyl-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-ylidene)amine N-oxide 
• 51549-65-6 N-benzyl-4-[1,2:3,4-di-O-isopropylidene-α-D-galactohexo-1,5-pyranose]methylene-imine 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 220172-62-3 (E)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenone 
• 77-71-4 5,5-dimethyl-imidazolidine-2,4-dione 
• 116730-74-6 5-(4,5-isopropylidene-L-gluconor-L-mannono-nitrile-6-yl)hydantoin 
• 116730-68-8 5-<1,2:3,4-di-O-isopropylidene-α-D-galacto-pentopyranose-5(R)-yl>hydantoin 
• 116730-54-2 6-deoxy-1,2:3,4-di-O-isopropylidene-6-ureido-DL-glycero-α-D-galacto-heptopyranuronamide 
• 245122-07-0 (Z)-(2'S,3'R,4'R,5'R,6'R)-2-[2'(3',4',5',6'-Di-O-isopropylidene)tetrahydropyranyl]-1-methoxy-1-phenylthio ethene 
• 76951-85-4 6,7-(N-benzyloxycarbonyl)epimino-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-β-L-glycero-D-galacto-heptopyranose 
• 99166-46-8 (2R,3R)-2-(6-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-α-D-galacto-1,5-pyranosyl)-3-benzyloxy-2,3-dihydro-4H-pyran-4-one 
• 116386-45-9 (E)-8-O-benzoyl-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-D-galacto-oct-6-enopyranose 

Relevant articles and documents

Synthesis and Conformational Analysis of (6R)--1,2:3,4-Di-O-isopropylidene-α-D-galactopyranose. NMR and Molecular Modeling Studies

The conformation preferences of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose have been determined using NMR and molecular modeling (conformational searching) techniques.The pyranose ring assumes a skew-boat conformation.Coupling constants for the C6 side chain and hydroxyl proton indicate that the predominant conformation places the oxygen anti to C4 (gt conformation) with the hydroxyl hydrogen aligned toward the pyranose oxygen in deuteriochloroform.A similar orientation of the C5-C6 bond was observed in water and toluene.In DMSO the C6 oxygen is anti to the pyranose oxygen (tg conformation) with the hydroxyl hydrogen anti to C5.A similar orientation of the C5-C6 bond was observed in methanol.

Synthesis and conformational properties of methyl 6,6-di-C-methyl-beta-D-galactopyranoside. Probes for the combining sites of D-galactosyl-binding proteins.

The binding of D-galactopyranosyl groups by lectins and antibodies can involve the 5-hydroxymethyl group. In order to examine the nature of these binding reactions, it was of interest to synthesize 6,6-di-C-methyl-D-galactose which was found to exist, like D-galactose, extensively in the pyranose forms. 2,3,4,6-Tetra-O-acetyl-7-deoxy-6-C-methyl-alpha-D-galacto-heptopyranosyl bromide was prepared under standard conditions and converted into methyl 6,6-di-C methyl-beta-D-galactopyranoside (6). Evidence based on 13C-n.m.r. studies indicates that the favored conformer of 6 has O-4 and O-6 in syn-axial-like relationship. General comments are presented on the nature of the binding of oligosaccharides by proteins.

The synthesis and conformational properties of the diastereoisomeric βDGal(1-4)βDGlcNAc(1-6)6-C-CH3-D-Gal trisaccharides

The trisaccharide βDGal(1->4)βDGlcNAc(1->6)DGal was known to be bound strongly by the so-called anti-I Ma monoclonal antibody.In order to help assess the conformation about the 1->6 glycosidic linkage that is accepted by the antibody combining site, the conformationally well-defined βDGal(1->4)βDGlcNAc(1->6) derivatives of 7-deoxy-L-glycero-D-galacto-heptopyranose and 7-deoxy-D-glycero-D-galacto-heptopyranose were synthesized.The conformational preferences for these trisaccharides were estabished by 1H nmr spectroscopy and rationalized by computer-assisted molecular modelling.

ANALOGS OF CELL SURFACE CARBOHYDRATES. SYNTHESIS OF D-GALACTOSE DERIVATIVES HAVING AN ETHYNYL, VINYL OR EPOXY RESIDUE AT C-5

Compounds derived from D-galactose having an ethynyl, vinyl, or epoxide residue at C-5, as well as 7,7-dibromo olefinic, isomeric 7,7-gem-bromofluoro olefinic, and 6,6-gem-difluoro derivatives were obtained from 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose.

Total Synthesis of β- D -ido-Heptopyranosides Related to Capsular Polysaccharides of Campylobacter jejuni HS:4

The 6-deoxy-β-d-ido-heptopyranoside related to the capsular polysaccharides of C. jejuni HS:4 is very remarkable, owing to the unique, multifaceted structural features that have been combined into one molecule, which include (1) the rare ido-configuration, (2) the unusual 7-carbon backbone, and (3) the challenging β-(1→2)-cis-anomeric configuration. Two distinct strategies toward the total synthesis of this interesting target are reported. The first involved establishment of the β-d-idopyranosyl configuration from β-d-galactopyranosides, prior to a C-6-homologation extending the d-hexose to the desired 6-deoxy-d-heptose. However, this approach encountered difficulties due to the significantly reduced reactivity of the 6-position of the β-d-idopyranosides, so instead a second strategy was employed, which involved first carrying out a 6-homologation on the less flexible d-galactopyranose, followed by a very successful conversion to the desired β-d-ido-configuration found in the target heptopyranoside (2). This report is the first successful synthesis of the 6-deoxy-β-d-ido-heptopyranoside, which could possess interesting immunological properties.

Multicomponent Approach to Homo-and Hetero-Multivalent Glycomimetics Bearing Rare Monosaccharides

We applied a multicomponent approach to access a library of densely functionalized homo-and hetero-multivalent glycomimetics comprising aldehyde, amine, and isocyanide components related to isopropylidene-protected d-fructose, l-sorbose, d-galactose, and d-Allose. Passerini products were obtained in very good yields (up to 78%) and high diastereoselectivities (up to 98:2). Three types of products were obtained by the Ugi reaction; along with the "classical" four-component product, α-Acylaminoamides, a three-component α-Aminoamides, and a four-component α-Aminoacylamides were isolated. The presence of multiple pathways is rationalized by the structure of the imidate intermediate, mainly influenced by the amine component.

N-Alkylated C-Glycosyl Amino Acid Derivatives: Synthesis by a One-Pot Four-Component Ugi Reaction

C-glycosides represent an important group of naturally occurring glycosylation derivatives but are also efficient mimetics of native O-glycosides. Here, a one-pot four-component methodology is described toward a library of N-alkylated C-glycosyl amino acid derivatives comprising seven different isopropylidene-protected carbohydrate units. The applied methodology tolerates different amines and isocyanides and provides access to Ugi products in yields up to 85 %. X-ray analysis of selected products bearing three different carbohydrate motifs and comparison of their crystal structures with similar ones deposited in Cambridge Crystallographic Database revealed that four structures adopt different conformations, mostly not typical for peptide structures. This property opens the possibility to exploit here described N-alkylated C-glycosyl amino acid derivatives as templates to access different biotic and abiotic secondary structures.