31795-13-8

Basic information

• Product Name: 1,2-O-ISOPROPYLIDENE-3-O-BENZOYL-D-ALLOFURANOSE
• Synonyms: 1,2-O-ISOPROPYLIDENE-3-O-BENZOYL-D-ALLOFURANOSE
• CAS NO: 31795-13-8
• Molecular Formula: C₁₆H₂₀O₇
• Molecular Weight: 324.33
• Mol File: 31795-13-8.mol

Chemical Properties

• Melting Point: 95-99 °C
• Boiling Point: 482.9°Cat760mmHg
• Flash Point: 176.1°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 3.88E-10mmHg at 25°C
• Refractive Index: 1.582
• PKA: 13.51±0.20(Predicted)
• CAS DataBase Reference: 1,2-O-ISOPROPYLIDENE-3-O-BENZOYL-D-ALLOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-ISOPROPYLIDENE-3-O-BENZOYL-D-ALLOFURANOSE(31795-13-8)
• EPA Substance Registry System: 1,2-O-ISOPROPYLIDENE-3-O-BENZOYL-D-ALLOFURANOSE(31795-13-8)

Safety Data

• Hazardous Substances Data: 31795-13-8(Hazardous Substances Data)

Usage

Type of Compound

Chemical compound

Function

Protecting group for hydroxyl functions in organic synthesis

Derivation

Derived from D-allofuranose

Isopropylidine group

Present at the 1 and 2 positions

Benzoyl group

Present at the 3 position

Synthesis of complex natural products and pharmaceuticals

Acts as a key intermediate

Protection of hydroxyl groups

Controls reactivity and selectivity during chemical transformations

Carbohydrate chemistry

Has applications in the field

Building block

Used for the preparation of glycosidic linkages in carbohydrate-based drugs and materials

InChI:InChI=1/C16H20O7/c1-16(2)22-13-12(11(10(18)8-17)21-15(13)23-16)20-14(19)9-6-4-3-5-7-9/h3-7,10-13,15,17-18H,8H2,1-2H3/t10?,11-,12-,13?,15?/m1/s1

Upstream product

• 98-88-4 benzoyl chloride 
• 286011-06-1 1,2:5,6-di-O-isopropylidene-α-D-galactofuranose 
• 29474-73-5 (+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 2595-05-3 Diacetone D-glucose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 613-90-1 benzoyl cyanide 
• 80667-81-8 1,2:5,6-di-O-isopropylidene-3-O-(N-imidazole-1-sulfonyl)-α-D-glucofuranose 
• 18819-89-1 tetrabutylammonium benzoate 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 

Downstream Products

• 31795-14-9 3-O-Benzoyl-1,2-O-isopropyliden-5,6-di-O-methylsulfonyl-α-D-allofuranose 
• 159043-21-7 3-O-Benzoyl-1,2-O-isopropyliden-6-O-(p-tolylsulfonyl)-α-D-allofuranose 
• 80890-30-8 (3R,4R,5R)-5-(2-Benzyloxy-ethyl)-4-methyl-tetrahydro-furan-2,3-diol 
• 80879-41-0 (3R,4S,5R)-4-Benzyloxymethyl-5-ethyl-tetrahydro-furan-2,3-diol 
• 80879-42-1 (2R,3R)-2-Benzyloxymethyl-3-hydroxy-pentanal 
• 80879-40-9 (3aR,5R,6R,6aR)-6-Benzyloxymethyl-5-ethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 80890-17-1 (E)-(4R,5R)-4-Benzyloxymethyl-5-hydroxy-2-methyl-hept-2-enoic acid ethyl ester 
• 80879-43-2 (E)-3-[(4S,5S,6R)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-acrylic acid ethyl ester 
• 80879-44-3 (R)-3-[(4S,5S,6R)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methyl-hex-5-enoic acid ethyl ester 
• 80879-44-3 (S)-3-[(4S,5S,6R)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-5-methyl-hex-5-enoic acid ethyl ester 
• 143504-33-0 3-O-Benzoyl-5-O-benzyloxymethyl-6-deoxy-1,2-O-isopropylidene-α-D-allofuranose 
• 143504-35-2 3-Azido-5-O-benzyloxymethyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 143504-32-9 3-O-Benzoyl-6-deoxy-1,2-O-isopropylidene-α-D-allofuranose 
• 143504-34-1 5-O-Benzyloxymethyl-6-deoxy-1,2-O-isopropylidene-α-D-allofuranose 

Relevant articles and documents

An alternative pathway to ribonucleoside β-hydroxyphosphonate analogues and related prodrugs

Nucleoside β-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5′-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reducti

A facile and practical synthesis of peracylated 4-thio-D-ribofuranoses from D-glucose

(Chemical Equation Presented) A practical synthesis of a peracylated 4-thio-D-ribofuranose 14 starting from inexpensive D-glucose is described. The C2-C6 portion of D-glucose was utilized, in which sulfur was introduced to C5 in two consecutive displacement reactions with net retention of configuration under mild conditions.

Ex-chiral-pool synthesis of β-hydroxyphosphonate nucleoside analogues

A new series of mononucleotide analogues bearing a nonhydrolysable P-C bond instead of the P-O phosphate linkage is presented. We intend to set up an approach that allows the synthesis of β-hydroxyphosphonate nucleoside analogues as a single diastereoisomer. In this respect, the key "sugar-phosphonate" intermediate was obtained through an Arbusov reaction from an iodosugar derivative in which the stereochemistry of the β-hydroxy group is determined by the choice of the starting material and remains in the resulting nucleotide analogues. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Nucleoside 5′-C-phosphonates: reactivity of the α-hydroxyphosphonate moiety

We found that various dialkyl phosphites, dialkyl trimethylsilyl phosphites, and tris-trimethylsilyl phosphite reacted smoothly with nucleoside 5′-aldehydes to afford epimeric nucleoside 5′-C-phosphonates in high yields. A number of these compounds in bot

Oxidative cleavage of ribofuranose 5-(α-hydroxyphosphonates): a route to erythrofuranose-based nucleoside phosphonic acids

We report here an oxidative cleavage of (5R)- and (5S)-ribofuranosyl-5-C-phosphonate derivatives with periodate anion under both strong acidic and neutral conditions. In both cases, only (5R)-configured compound underwent the expected oxidation reaction a

Synthesis and properties of RNA analogues having amides as interuridine linkages at selected positions

Oligoribonucleotide analogues having amide internucleoside linkages (AM1: 3′-CH2CONH-5′ and AM2: 3′-CH 2NHCO-5′) at selected positions have been synthesized and the thermal stability of duplexes formed by these analogues with complem

A one-pot strategy for synthesis of 5-O-(α-D-Arabinofuranosyl)-6-O-(β-D-galactofuranosyl)-D- galactofuranose present in motif E of the Mycobacterium tuberculosis cell wall

5-O-(α-D-Arabinofuranosyl)-6-O-(β-D-galactofuranosyl)-D- galactofuranose 6 present in motif E of the Macobacterium tuberculosis cell wall has been regio- and stereospecifically synthesized using 3-O-benzoyl-1,2-O-isopropylidine-α-D-galactofuranose (10) as the glycosyl acceptor by the trichloroacetamidate method in a one-pot manner. The diol glycosyl acceptor 10 was smoothly derived from 1,2:5,6-di-O-isopropylidene-α-D-galactofuranose (8) by 3-O-benzoylation and then selective 5,6-O-deacetonation. The preparation of 8 was greatly improved by increasing the ratio of DMF to acetone and using a solid-supported catalyst.

Homologues of isomeric dideoxynucleosides as potential antiviral agents: Synthesis of isodideoxy-nucleosides with a furanethanol sugar moiety

The synthesis of a homologues series of compounds related to (R, S)- isodideoxynucleosides has been completed by coupling a variety of natural purine and pyrimidine bases with a modified sugar intermediate. This sugar precursor was prepared regiospecifica

An Efficient Synthesis of Enantiomeric Ribonucleic Acids from D-Glucose

Enantiomeric oligoribonucleotides ( = ent-RNA) up to a sequence length of thirty-five and consisting of the (L-configurated) nucleosides ent-adenosine, ent-guanosine, ent-cytidine, ent-uridine, and 1-(β-L-ribofuranosyl)thymine were prepared by automated synthesis from appropriate building blocks, carrying a known photolabile 2′-O-protecting group. A simple large-scale synthesis of the new, prefunctionalized L-ribose derivative 5 from D-glucose (Scheme 1) and its straightforward conversion into the five phosphoramidites 28-32 and five solid supports 38-42, respectively, were elaborated (Scheme 4). Within this project, a novel, superior strategy for the synthesis of the 2′-O-{[(2-nitrobenzyl)oxy]methyl}-substituted key intermediates 18-22 by regioselective alkylation of their 5′-O-dimethoxytritylated precursors 13-17 was developed. Furthermore, an improved set-up for the final light-induced cleavage of the 2′-O-protecting groups from the oligonucleotide sequences was designed (Scheme 5 and Fig. 1). The correct composition of all ent-oligoribonucleotides prepared was established by their MALDI-TOF mass spectra. The 1H-NMR-spectroscopic data of a dodecameric ent-RNA sequence was in excellent agreement with the published data of its natural counterpart, synthesized by conventional methods. The known specific cleavage of a tetradecamer sequence by a 35mer ribozyme structure could be reproduced by ent-oligoribonucleotides, synthesized by the presented methods (Fig. 4).

Synthesis, Structure Elucidation and Reactions of trans-Fused 3,6-Anhydro-1,2-O-isopropylidene-α-D-hexofuranoses

Unexpectedly, the reaction of 1,2-O-isopropylidene-5,6-di-O-(p-tolylsulfonyl)-α-D-allofuranose (7) with KCN in ethanol yielded the first trans-fused 3,6-anhydro-hexofuranose 10.Besides by spectroscopic evidence the structure of 10 was proved by transformation to the tosylated acetal 13 which could also be obtained via an independent route.Further reactions of 10 all resulted in opening of the strained ring system yielding acetals (18-22).By blocking the 5-position with the alkali-resistant ether function this cyclization could also be achived by more common reagents like NaH in DMF (32). - By applying this procedure to the corresponding α-D-galactofuranose derivative 41 3,6-anhydro-α-D-galactofuranose 42 could also be obtained albeit in low yield.For comparison purposes the 3,6-anhydro-α-D-gulo derivative 47 was synthesized from easily accessible 44. - Key Words: Carbohydrates / Hexofuranoses / 3,6-Anhydro-D-hexofuranoses