5627-19-0

Basic information

• Product Name: 1,4:3,6-Dianhydro-L-iditol
• Synonyms: 1,4:3,6-Dianhydroiditol;1,4:3,6-Dianhydro-L-iditol;Isoidide;L-Isoidide;(3S,3aR,6S,6aR)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol
• CAS NO: 5627-19-0
• Molecular Formula: C₆H₁₀O₄
• Molecular Weight: 146.14
• Mol File: 5627-19-0.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,4:3,6-Dianhydro-L-iditol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4:3,6-Dianhydro-L-iditol(5627-19-0)
• EPA Substance Registry System: 1,4:3,6-Dianhydro-L-iditol(5627-19-0)

Safety Data

• Hazardous Substances Data: 5627-19-0(Hazardous Substances Data)

Usage

Type of compound

Cyclic sugar alcohol

Structure

A cyclic sugar alcohol derived from L-iditol, a sugar alcohol found in nature

Molecular weight

146.14 g/mol

Appearance

White crystalline solid

Solubility

Soluble in water, slightly soluble in organic solvents like ethanol and methanol

Melting point

95-97°C

Boiling point

Not readily available, but expected to be high due to its cyclic structure and polarity

Density

Not readily available, but expected to be relatively high due to its molecular weight and structure

Optical activity

Exhibits optical isomerism, with both D and L forms existing

Applications

Building block in the synthesis of pharmaceutical and natural products
Precursor in the production of various drugs
Intermediate in the preparation of cyclic compounds
Chiral resolving agent in chromatography
Starting material for the synthesis of organic molecules

Safety

Handle with care, as it may cause irritation to the eyes, skin, and respiratory system

Storage

Store in a cool, dry place, away from direct sunlight and moisture

Stability

Stable under normal conditions, but may decompose upon exposure to heat, light, or moisture

Reactivity

Reacts with various reagents to form different derivatives, which can be used in the synthesis of various compounds

Environmental impact

Low toxicity, but proper disposal is recommended to minimize environmental impact

Regulatory status

Not classified as a hazardous substance, but safety precautions should be taken during handling and storage

Research interest

Gained interest in various fields due to its unique structural properties and potential applications in pharmaceuticals, natural products, and organic synthesis

Upstream product

• 641-74-7 1,4:3,6-dianhydro-D-mannitol 
• 652-67-5 Isosorbide 
• 24808-18-2 di-O-acetyl-1,4;3,6-dianhydro-L-iditol 
• 3014-56-0 (3S,3aR,6S,6aR)-6-(benzoyloxy)hexahydrofuro[3,2-b]furan-3-yl benzoate 
• 67-56-1 methanol 
• 2914-23-0 barium methoxide 
• 54522-28-0 1,4:3,6-dianhydro-2,5-di-O-p-tosyl-D-iditol 
• 470-15-5 α-L-sorbopyranose 
• 7647-01-0 hydrogenchloride 
• 48107-55-7 (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diamine 
• 64-17-5 ethanol 
• 488-45-9 L-iditol 
• 7664-93-9 sulfuric acid 
• 54522-28-0 (3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate) 

Downstream Products

• 3014-56-0 (3S,3aR,6S,6aR)-6-(benzoyloxy)hexahydrofuro[3,2-b]furan-3-yl benzoate 
• 24808-19-3 (3S,3aS,6S,6aS)-6-[(methylsulfonyl)oxy]hexahydrofuro[3,2-b]furan-3-yl methanesulfonate 
• 54522-28-0 1,4:3,6-dianhydro-2,5-di-O-p-tosyl-D-iditol 
• 103536-93-2 2-O-Allyl-isomannide 
• 6338-34-7 (3S,3aS,6S,6aS)-3,6-Bis-allyloxy-hexahydro-furo[3,2-b]furan 
• 103617-84-1 2-O-allyl-1,4:3,6-dianhydro-L-iditol 
• 6338-34-7 (3S,3aR,6S,6aR)-3,6-Bis-allyloxy-hexahydro-furo[3,2-b]furan 
• 1201908-67-9 (3S,3aS,6S,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate 
• 1353755-28-8 2,5-(benzylimino)-2,5-dideoxy-1,4:3,6-dianhydro-D-mannitol 
• 1453124-78-1 C₂₄H₁₈F₁₂N₄O₂S₂ 

Relevant articles and documents

Direct Amination of Isohexides via Borrowing Hydrogen Methodology: Regio- and Stereoselective Issues

The regio and diastereoselective direct mono or diamination of bio-based isohexides (isosorbide and isomannide) has been developed through borrowing hydrogen (BH) methodology using a cooperative catalysis between an iridium complex and a Br?nsted acid. The access to chiral amino-alcohol (NH2-OH) and diamine (NH2-NH2), interesting optically pure bio-based monomers, was also proposed using BH strategy as a sustainable route for their obtention.

Is water a suitable solvent for the catalytic amination of alcohols?

The catalytic conversion of biomass and biogenic platform chemicals typically requires the use of solvents. Water is present already in the raw materials and in most cases a suitable solvent for the typically highly polar substrates. Hence, the development of novel catalytic routes for further processing would profit from the optimization of the reaction conditions in the aqueous phase mainly for energetic reasons by avoiding the initial water separation. Herein, we report the amination of biogenic alcohols in aqueous solutions using solid Ru-based catalysts and ammonia as a reactant. The influence of different support materials and bimetallic catalysts is investigated for the amination of isomannide as a biogenic diol. Most importantly, the transferability of the reaction conditions to various other primary and secondary alcohols is successfully proved. Hence, water appears to be a suitable solvent for the sustainable production of biogenic amines and offers great potential for further process development.

ISOIDIDE MANUFACTURE AND PURIFICATION

Methods are provided for the conversion of isosorbide to isoidide, wherein the isosorbide contains sorbitan impurities. The impurities in the isosorbide subjected to epimerization are converted to hydrodeoxygenation products. A method for synthesizing isoidide, comprising, providing an isosorbide containing one or more sorbitans; and, epimerizing the isosorbide to form an epimerization product comprising isoidide and hydrodeoxygenation products.