19139-74-3

Usage

Uses

Used in Organic Synthesis:
2,3:4,5-Di-O-isopropylidene-D-arabinitol is used as a protecting group for diols in organic synthesis. Its ability to protect diols from unwanted reactions allows for selective functionalization of other groups in a molecule, facilitating the synthesis of complex organic compounds.
Used in Pharmaceutical Synthesis:
IPDA serves as a precursor in the synthesis of various pharmaceuticals and natural products. Its unique structure and reactivity enable the development of new and innovative drugs with potential therapeutic applications.
Used in Carbohydrate Chemistry:
2,3:4,5-Di-O-isopropylidene-D-arabinitol is used in the preparation of carbohydrate derivatives. Its ability to protect hydroxyl groups in carbohydrates allows for the selective modification of these biomolecules, leading to the development of new carbohydrate-based compounds with potential applications in various fields.
Used as a Building Block in Organic Synthesis:
IPDA is utilized as a building block in the synthesis of complex organic molecules. Its unique structure and reactivity make it a valuable component in the construction of intricate organic compounds, contributing to the advancement of organic chemistry.
Used in Research:
2,3:4,5-Di-O-isopropylidene-D-arabinitol is an important reagent in organic chemistry research. Its unique properties and reactivity make it a valuable tool for studying various chemical reactions and mechanisms, contributing to the understanding and development of new synthetic methods and strategies.
Overall, 2,3:4,5-Di-O-isopropylidene-D-arabinitol, or IPDA, is a versatile and valuable compound in the field of organic chemistry, with applications spanning from pharmaceutical synthesis to research and development of new organic compounds. Its unique structure and reactivity make it an essential component in various chemical processes and a promising candidate for the development of innovative applications.

Upstream product

• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 10323-20-3 D-Arabinose 
• 88367-63-9 (1S,2S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propane-1,2-diol 
• 50-69-1 D-ribose 
• 70337-20-1 2,3:4,5-di-O-isopropylidene-D-ribose diethyl dithioacetal 
• 77-76-9 2,2-dimethoxy-propane 
• 69977-54-4 D-O²,O³-isopropylidene-ribitol 
• 220172-58-7 (E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol 
• 87-99-0 XYLITOL 
• 67-64-1 acetone 
• 7152-47-8 D-ribose diethyl dithioacetal 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 81769-41-7 (2R,3S,4R)-5-(Phenylthio)-1,2-O-isopropylidenepentane-1,2,3,4-tetrol 
• 146986-66-5 (S)-4,5-isopropylidenedioxy-2-pentenol 

Downstream Products

• 71769-38-5 1-deoxy-2,3-o-isopropylidene-1-tosyl-D-arabinitol 
• 267873-86-9 1,2:3,4-di-O-isopropylidene-5-O-p-methoxybenzyl-D-lyxitol 
• 488-82-4 D-Arabitol 
• 19139-73-2 (4S,4’R,5R)-5-[(benzyloxy)methyl]-2,2,2’,2’-tetramethyl-4,4’-bis[1,3-dioxolane] 
• 869660-95-7 1-O-benzyl-2,3-O-isopropylidene-4-oxiranyl-D-arabinitol 
• 869660-96-8 (2R,3R,4R)-1-O-benzyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3,4-tetrol 
• 869660-97-9 (2R,3R,4S)-4-azido-1-O-benzyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol 
• 869660-99-1 (2R,3R,4S)-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol 
• 1053622-69-7 Methanesulfonic acid (4R,5R)-5-[(S)-1-tert-butoxycarbonylamino-2-(4-methoxy-phenyl)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 869660-98-0 (2R,3R,4S)-1-O-benzyl-4-(tert-butoxycarbonyl)amino-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol 
• 19713-95-2 (2S,3R,4R)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 
• 111765-92-5 (2S,3R,4R)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 
• 346588-20-3 1-O-benzyl-2,3-O-(1-methylethylidene)-D-arabinitol 
• 81801-09-4 4-O-benzyl-2,3-O-isopropylidene-D-threose 

Relevant academic research and scientific papers

Surgical Cleavage of Unstrained C(sp3)?C(sp3) Bonds in General Alcohols for Heteroaryl C?H Alkylation and Acylation

We reported herein a predictable and surgical cleavage of carbon-carbon bond in alcohols. A wide range of 1°, 2° and 3° alcohols including sugars and steroids without ring strain or steric hindrance were all compatible with this system. Also it offered a green and practical strategy for generation of alkyl/acyl radicals using alcohols as the sources. Besides, the features of visible-light-initiation, catalyst and metal free, excellent selectivity and mild conditions make it valuable and attractive. (Figure presented.).

Towards stereoselective synthesis of the C(31)-C(39) and C(20)-C(27) fragments of phorboxazole A

The stereoselective synthesis of the C(31)-C(39) and C(20)-C(27) fragments of phorboxazole A (1) was achieved from commercially available and inexpensive D-mannitol. Crimmins aldol reaction and a decarboxylative Claisen-type reaction are the key steps for

A facile and stereoselective synthesis of the C-2 epimer of (+)-deacetylanisomycin

A short, simple and efficient synthesis of the C-2 epimer of (+)-deacetylanisomycin starting from d-mannitol, utilizing an epoxide opening with a Grignard reagent and acid catalysed unusual intramolecular 5-endo-tet cyclization as key steps has been repor

The Baylis-Hillman reaction: a strategic tool for the synthesis of higher-carbon sugars

The Baylis-Hillman reaction of acyclic sugar-derived aldehydes is invoked as an attractive synthetic strategy for ready access to higher-carbon sugars.

Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: Total synthesis of acremoauxin A and oxazinin 3

Full details are provided for a recently invented method to couple indoles and pyrroles to carbonyl compounds. The reaction is ideally suited for structurally complex substrates and exhibits high levels of chemoselectivity (functional group tolerability), regioselectivity (coupling occurs exclusively at C-3 of indole or C-2 of pyrrole), stereoselectivity (substrate control), and practicality (amenable to scaleup). In addition, quaternary stereocenters are easily and predictably generated. The reaction has been applied to a number of synthetic problems including total syntheses of members of the hapalindole family of natural products, ketorolac, acremoauxin A, and oxazinin 3. Mechanistically, this coupling protocol appears to operate by a single electron-transfer process requiring generation of an electron-deficient radical adjacent to a carbonyl which is then intercepted by an indole or pyrrole anion.

Stereoselective synthesis of (3S,8R,9R,10R)-heptadeca-1-ene-4,6-diyne tetrol and its 3-epimer from D-mannitol

(3S,8R,9R,10R)-Heptadeca-1-ene-4,6-diyne tetrol and its 3-epimer were synthesized, and it was found that the relative configuration which was proposed for 1 was incorrect. Georg Thieme Verlag Stuttgart.

Total synthesis of aspinolide B: a ring-closing metathesis approach

A highly convergent stereoselective total synthesis of aspinolide B, a 10-membered lactone is described. The key step includes a ring-closing metathesis reaction to construct the 10-membered ring and the E-olefinic moiety. d-Mannitol was used as a chiral

A new approach to (+)-anisomycin

An efficient approach to enantiomerically pure (+)-deacetylanisomycin 2a and a formal synthesis of (+)-anisomycin 2 (11% overall yield in 10 steps) have been achieved through simple and good yielding reactions, starting from 1,2:3,4:5,6-tri-O-isopropylidene-D-mannitol 3. Grignard reaction and intramolecular cyclisation reactions are key steps in the strategy.

Reaction of sugar allyltins with aldehydes. A remarkable difference in reactivity between furanose and pyranose organometallic derivatives

The reaction of organometallic derivatives of monosaccharides with aldehydes catalyzed with BF3·OEt2 was studied. A significant difference in reactivity between the pyranosidic and furanosidic and allyltins was noted. The former reacted readily with aldehydes affording precursors of higher carbon sugars with very high stereoselectivity, while the latter underwent rearrangement with elimination of the stannyl moiety prior to reaction with the aldehyde.