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

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

Purpose

Used in organic synthesis and carbohydrate chemistry

Derivative of

D-galactose

Function

Commonly used as a protecting group for hydroxyl groups in carbohydrates

Physical appearance

White to off-white powder

Molecular weight

288.34 g/mol

Melting point

Around 140-143°C

Solubility

Soluble in various organic solvents such as acetone and ethyl acetate

Applications

Important in the development of new drugs, 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 
• 118920-26-6 C₂₃H₂₀O₈ 
• 118893-76-8 C₂₆H₂₄O₈ 
• 1010075-67-8 C₁₅H₂₄O₅S₂ 
• 108678-44-0 tert-butyldimethyl(2,2,7,7-tetramethyltetrahydrobis[1,3]dioxolo[5,4-b:4',5'-d]pyran-5-ylmethoxy)silane 
• 3646-73-9 α-D-galactopyranose 
• 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 
• 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 
• 59-23-4 D-Galactose 
• 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 

Downstream Products

• 18524-41-9 (3aR,5S,5aR,8aS,8bR)-methyl-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-carboxylate 
• 132556-30-0 (3aR,5R,5aS,8aS,8bR)-5-((Z)-2-Benzenesulfonyl-2-fluoro-vinyl)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 132556-29-7 (3aR,5R,5aS,8aS,8bR)-5-((E)-2-Benzenesulfonyl-2-fluoro-vinyl)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 109200-85-3 (S)-((S)-1-Phenyl-ethylamino)-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-acetonitrile 
• 109200-86-4 (R)-((S)-1-Phenyl-ethylamino)-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-acetonitrile 
• 77312-91-5 (E)-1-(3-Nitro-phenyl)-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)-propenone 
• 124342-34-3 (3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-5-(4-methylene-3-phenyl-tetrahydro-furan-2-yl)-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 135822-99-0 4-Methyl-N-[(3aR,5aR,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-(5E)-ylidenemethyl]-benzenesulfonamide 
• 92524-95-3 Benzoic acid (2S,3R)-4-oxo-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-3,4-dihydro-2H-pyran-3-yl ester 
• 137845-11-5 (3aR,5S,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-5-(4-methylene-3-phenylsulfanyl-tetrahydro-furan-2-yl)-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 80564-76-7 9,10-Di-O-benzyl-1,2;3,4-di-O-isopropyliden-11-O-trityl-D-manno-α-D-galacto-7-undeculopyranose-trimethylendithioacetal 
• 152574-30-6 7-Deoxy-1,2:3,4-di-O-isopropylidene-7-(phenyldimethylsilyl)-D-glycero-α-D-galacto-heptopyranose 
• 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 

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 Biological Evaluation of 6-[(1 R)-1-Hydroxyethyl]-2,4a(R),6(S),8a(R)-tetrahydropyrano-[3,2- b]-pyran-2-one and Structural Analogues of the Putative Structure of Diplopyrone

The phytotoxin diplopyrone is considered to be the main phytotoxin in a fungus that is responsible for cork oak decline. A carbohydrate-based synthesis of the enantiomer of the structure proposed for diplopyrone has been developed from a commercially available derivative of d-galactose. Key steps in the synthesis are a highly stereoselective pyranose chain-extension based on methyltitanium, preparation of a vinyl glycoside via Isobe C-alkynylation-rearrangement/reduction, and RCM-based pyranopyran construction. Crystallographic and NMR analysis confirms an earlier report that the structure originally proposed for diplopyrone may require revision. Structural analogues were prepared for biological evaluation, the most promising being a pyranopyran nitrile synthesized from tri-O-acetyl-d-galactal by Ferrier cyanoglycosidation, Wittig chain extension, and lactonization. Biological assays revealed potent antibacterial activity for the nitrile analogue against common bacterial pathogens Edwardsiella ictaluri and Flavobacterium columnare that cause enteric septicemia (ESC) and columnaris disease, respectively, in catfish. The IC50 value of 0.002 against E. ictaluri indicates approximately 100 times greater potency than the antibiotic florfenicol used commercially for this disease. Phytotoxic activity for all three target compounds against duckweed was also observed. The antibiotic and phytotoxic activities of the new pyranopyrans synthesized in this study demonstrate the potential of such compounds as antibiotics and herbicides.

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.

Biocatalytic Production of Amino Carbohydrates through Oxidoreductase and Transaminase Cascades

Plant-derived carbohydrates are an abundant renewable resource. Transformation of carbohydrates into new products, including amine-functionalized building blocks for biomaterials applications, can lower reliance on fossil resources. Herein, biocatalytic production routes to amino carbohydrates, including oligosaccharides, are demonstrated. In each case, two-step biocatalysis was performed to functionalize d-galactose-containing carbohydrates by employing the galactose oxidase from Fusarium graminearum or a pyranose dehydrogenase from Agaricus bisporus followed by the ω-transaminase from Chromobacterium violaceum (Cvi-ω-TA). Formation of 6-amino-6-deoxy-d-galactose, 2-amino-2-deoxy-d-galactose, and 2-amino-2-deoxy-6-aldo-d-galactose was confirmed by mass spectrometry. The activity of Cvi-ω-TA was highest towards 6-aldo-d-galactose, for which the highest yield of 6-amino-6-deoxy-d-galactose (67 %) was achieved in reactions permitting simultaneous oxidation of d-galactose and transamination of the resulting 6-aldo-d-galactose.

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.

Synthesis, characterization and cytotoxicity of cyclopentadienyl ruthenium(II) complexes containing carbohydrate-derived ligands Dedicated to Prof. Maria José Calhorda on the occasion of her 65th birthday.

We here report the synthesis of new cyclopentadienyl ruthenium(II) complexes of general formula [(η5-C5H 5)Ru(PP)(L)]+ (PP = two triphenylphosphine, 1,2-diphenylphosphinoethane), isolated as PF6- salts, with L b

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.

Methods Of Making Pyranopyrans Such As Pyranopyran Nitrile And Methods of Using Pyranopyrans Such As Pyranopyran Nitrile

Disclosed herein are methods of making (4aR,6S,8aR)-6-((R)-1-hydroxyethyl)-6,8a-dihydropyrano[3,2-b]pyran-2-(4aH)-one (2) and methods of making (4aR,6S,8aR)-6-cyano-6,8a-dihydropyrano-[3,2-b]pyran-2(4aH)-one (4). Other pyranopyrans were also synthesized. Also compositions containing (4aR,6S,8aR)-6-cyano-6,8a-dihydropyrano-[3,2-b]pyran-2(4aH)-one (4) (or other pyranopyrans described herein) and optionally a carrier. In addition, methods for killing microorganisms or weeds on or in an object or area involving contacting the object or area with an effective microorganisms or weeds killing amount of a composition containing (4aR,6S,8aR)-6-cyano-6,8a-dihydropyrano-[3,2-b]pyran-2(4aH)-one (4) (or other pyranopyrans described herein) and optionally a carrier.