4495-04-9

Usage

Chemical compound

1,2-O-Isopropylidene-D-allofuranose is a chemical compound.

Common use

It is commonly used in organic chemistry.

Purpose

It is used as a protecting group for aldehydes.

Derivative

It is a derivative of D-allose, a rare sugar.

Potential applications

D-allose has potential applications in pharmaceuticals and as a chiral building block for the synthesis of complex molecules.

Selective addition

1,2-O-Isopropylidene-D-allofuranose can be selectively added to aldehydes to prevent undesired reactions.

Easy removal

It can be easily removed under mild conditions to regenerate the original aldehyde functionality.

Importance in organic synthesis

1,2-O-Isopropylidene-D-allofuranose is an important tool in organic synthesis for controlling the reactivity and selectivity of aldehyde groups.

Widespread use

It has found widespread use in the preparation of various natural products and pharmaceutical compounds.

InChI:InChI=1/C9H16O6/c1-9(2)14-7-5(12)6(4(11)3-10)13-8(7)15-9/h4-8,10-12H,3H2,1-2H3/t4?,5-,6-,7?,8?/m1/s1

Upstream product

• 38166-60-8 1,2:5,6-di-O-isopropylidene-α-L-glucofuranoside 
• 1990-29-0 D-altrose 
• 67-64-1 acetone 
• 620630-82-2 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose 
• 329899-64-1 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 1392131-82-6 N-benzyl-6-O-tert-butyldimethylsilyl-3,5-dideoxy-3,5-imino-1,2-O-isopropylidene-alpha-D-gulofuranose 
• 1392131-83-7 N-benzyl-2,4-dideoxy-2,4-imino-D-glucitol 
• 1392131-84-8 (2E)-methyl-(4R,5R,6R,7S)-N-benzyl-4,6,8-trihydroxy-5,7-iminooct-2-enoate 
• 1392131-86-0 (2E)-methyl-(4R,5R,6R,7S)-N-benzyl-4,6,8-tris(tert-butyldimethylsilyloxy)-5,7-iminooct-2-enoate 
• 63846-98-0 1,2-O-(1-Methylethylidene)-α-D-ribo-pentodialdo-1,4-furanose 
• 217089-44-6 (3aR,5R,6R,6aR)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 113273-96-4 (1R,6R,8R,9R)-3-(benzoyloxy)-8,9-(isopropylidenedioxy)-7-oxabicyclo<4.3.0>nonane 
• 26532-02-5 1,2-O-isopropylidene-6-O-trityl-α-D-allofuranose 
• 55085-33-1 1-(O²-acetyl-O³,O⁶-dibenzoyl-β-D-ribo-5-deoxy-hexofuranosyl)-4-acetylamino-1H-pyrimidin-2-one 
• 55085-34-2 homocytidine 
• 88238-35-1 5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-ribo-hexofuranose 
• 88238-38-4 1-(5-deoxy-β-D-arabino-hexofuranosyl)cytosine 
• 88238-34-0 5,6-dideoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-ribo-hex-5-enofuranose 
• 88270-97-7 1,2-di-O-acetyl-3,6-di-O-benzoyl-5-deoxy-D-ribo-hexofuranose 

Relevant academic research and scientific papers

Synthesis from d-altrose of (5 R,6 R,7 R,8 S)-5,7-dihydroxy-8- hydroxymethylconidine and 2,4-dideoxy-2,4-imino-d-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-d-mannitol

Ring closure of a 3,5-di-O-triflate derived from d-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine.

Useful methods for the synthesis of isopropylidenes and their chemoselective cleavage

A catalytic amount of phosphotungstic acid (PTA) has been found to be a very effective catalyst for isopropylidenation of 1,2-diols and their deprotection at room temperature. The ease of handling, cost and activity of the catalyst, good to excellent yields and chemoselectivity for deprotection are some of the highlights of the reported method.

SYNTHESES OF 1-(5-DEOXY-Β-D-arabino-HEXOFURANOSYL)CYTOSINE

1-(5-Deoxy-β-D-arabino-hexofuranosyl)cytosine (4'-homoara-C) (11), a higher homolog of the antileukemic agent ara-C(1-β-D-arabinofuranosylcytosine), was prepared by two independent routes.The first one involved the inversion of configuration at C-2' of the D-ribo epimer (1-(5-deoxy-β-D-ribo-hexofuranosyl)cytosine, 4'-homocytidine) by the diphenylcarbonate technique; the 5-deoxy-D-ribo-hexofuranosyl moiety of 4'-homocytidine was obtained by way of an anti-Markovnikov addition of iodine trifluoroacetate to the double bond of 5,6-dideoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-ribo-hex-5-enofuranose and reduction of the resulting iodide(s).In the second approach, 5-deoxy-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-β-D-xylo-hexofuranose was acetolyzed and condensed with 4-acetyl-N-bis(trimethylsilyl)cytosine, and alkaline treatment gave 11 by way of a 2',3'-anhydro intermediate.The structure of 11, in particular the configuration at C-2', was confirmed by its 1H- and 13C-n.m.r. spectra.