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

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

• 100-46-9 benzylamine 
• 652-67-5 Isosorbide 
• 641-74-7 1,4:3,6-dianhydro-D-mannitol 
• 50-70-4 D-sorbitol 
• 616-38-6 carbonic acid dimethyl ester 
• 54522-28-0 (3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate) 
• 488-45-9 L-iditol 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 
• 7647-01-0 hydrogenchloride 
• 48107-55-7 (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diamine 
• 470-15-5 α-L-sorbopyranose 
• 67-56-1 methanol 
• 2914-23-0 barium methoxide 

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 
• 1453124-78-1 C₂₄H₁₈F₁₂N₄O₂S₂ 
• 1353755-28-8 2,5-(benzylimino)-2,5-dideoxy-1,4:3,6-dianhydro-D-mannitol 

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.

Unravelling the Mechanism of the Ru/C-Catalysed Isohexide and Ether Isomerization by Hydrogen Isotope Exchange

In this article we show that the catalytic isomerization of isohexide sugar alcohols as well as their respective ethers can occur by a hydride-based mechanism rather than a dehydrogenation/re-hydrogenation. C?H bonds in α-position to hydroxy and ether groups are activated using Ru/C as solid catalyst at temperatures as high as 160 °C and above. Hydrogen isotope exchange experiments proved that a full hydride exchange and isomerization is possible for isohexides but unexpectedly also for their methyl ethers. This is of great importance as it proves the co-existence of the both mechanisms for reactions that were so far assumed to occur solely by a dehydrogenation/re-hydrogenation. Hence, this co-existence should be taken into account for kinetic investigations of such reaction systems especially in the conversion of biomass-based chemicals under hydrogenation conditions. (Figure presented.).

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.

One-Pot Preparation of Dimethyl Isosorbide from d-Sorbitol via Dimethyl Carbonate Chemistry

Direct synthesis of dimethyl isosorbide (DMI) from d-sorbitol via dimethyl carbonate (DMC) chemistry is herein first reported. High yield of DMI was achieved using the nitrogen superbase 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as catalyst and performing the reaction in a stainless steel autoclave by increasing the temperature from 90 to 200 °C. In this procedure, DMC features its full capacity acting in the different steps of the process as carboxymethylating, leaving-group (cyclization), and methylating agent; DMC is also employed as the reaction media.

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.

METHOD OF MAKING ISOIDIDE

Disclosed is a process for the preparation of isoidide from isosorbide. An aqueous solution of isosorbide is subjected to epimerization in the presence of hydrogen under the influence of a catalyst comprising ruthenium on a support, preferably a carbon support. The process of the invention can be conducted using a relatively low hydrogen pressure, and leads to a desired distribution of epimers, favoring isoidide over isomannide and isosorbide.

Sustainable polyacetals from isohexides

A single step synthetic protocol to access a small family of renewable diacetals was established. The resultant chiral diacetals are valuable building blocks in pharmaceuticals and materials science. To demonstrate their synthetic competence, isohexide-diacetals (2a-c) were subjected to acetal metathesis polymerization and the corresponding polymers (poly2a-c) were isolated as white solids with molecular weights in the range 3200-27 600 (g mol-1). The semi-crystalline polymers displayed glass transition temperatures between 38-65 °C and melting temperatures in the range 103-156 °C. The isohexide derived polyacetals are stable under practical washing and rinsing conditions but degrade in slightly acidic media. This journal is the Partner Organisations 2014.

Direct amination of bio-alcohols using ammonia

A slightly adapted catalyst system has been successfully applied in the direct amination of primary and secondary alcohols. Moreover, the applicability to diols has been shown, giving high selectivity towards the primary diamines. It was found that the Ru/P ratio as well as the amount of ammonia used are highly important in this system, especially for higher substrate loadings. The catalyst was employed on a larger batch scale for the conversion of isomannide to the corresponding diamine. Additionally, it was shown that the catalyst is stable for at least six consecutive runs. No significant loss of activity and selectivity was observed.

Isolation of anhydro sugar hexitols by selective adsorbents

A method is disclosed for recovering anhydrosugar alcohols from a mixture comprising closely related compounds, such as sugar alcohols. In the method the mixture is contacted with an adsorbent, whereby the anhydrosugar alcohols are selectively adsorbed. The anhydrosugar alcohols can be recovered by desorption from the adsorbent, using a desorbing solvent.

ISOLATION OF ANHYDRO SUGAR ALCOHOLS BY SELECTIVE ADSORBENTS

A method is disclosed for recovering anhydrosugar alcohols from a mixture comprising closely related compounds, such as sugar alcohols. In the method the mixture is contacted with an adsorbent, whereby the anhydrosugar alcohols are selectively adsorbed. The anhydrosugar alcohols can be recovered by desorption from the adsorbent, using a desorbing solvent.