13042-39-2

Basic information

• Product Name: 1,4:3,6-Dianhydro-D-glucitol 2-acetate
• Synonyms: 1,4:3,6-dianhydro-D-glucitol 2-acetate;(6-Hydroxy-2,3,3a,5,6,6a-hexahydrofuro[2,3-d]furan-3-yl) acetate;Acetic acid (3S,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl ester;(6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl) acetate;(6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl) ethanoate;acetic acid (6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl) ester;2-Acetyl-isosorbide;1,4:3,6-Dianhydro-2-O-acetyl-D-glucitol
• CAS NO: 13042-39-2
• Molecular Formula: C8H12O5
• Molecular Weight: 188.18
• EINECS: 235-917-7
• Mol File: 13042-39-2.mol
• Article Data: 23

Chemical Properties

• Melting Point: 78 °C
• Boiling Point: 322.976 °C at 760 mmHg
• Flash Point: 132.52 °C
• Appearance: /
• Density: 1.348 g/cm³
• Vapor Pressure: 2.13E-05mmHg at 25°C
• Refractive Index: 1.51
• PKA: 13.35±0.40(Predicted)
• CAS DataBase Reference: 1,4:3,6-Dianhydro-D-glucitol 2-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4:3,6-Dianhydro-D-glucitol 2-acetate(13042-39-2)
• EPA Substance Registry System: 1,4:3,6-Dianhydro-D-glucitol 2-acetate(13042-39-2)

Safety Data

• Hazardous Substances Data: 13042-39-2(Hazardous Substances Data)

Usage

Uses

1,4:3,6-Dianhydro-2-O-acetyl-D-glucitol is a useful reagent in the practical enzymic synthesis of isosorbide-2-acetate.

InChI:InChI=1/C8H12O5/c1-4(9)13-6-3-12-7-5(10)2-11-8(6)7/h5-8,10H,2-3H2,1H3

Synthetic route

[(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate (13042-38-1) → isosorbide 2-acetate (13042-39-2)

Conditions	Yield
In acetone for 288h; Ambient temperature; lipase from Pseudomonas sp. (SAM II);	91%
With Novozym 435; sodium hydrogencarbonate In aq. phosphate buffer at 50℃; for 12h; pH=6; Catalytic behavior; Reagent/catalyst; Temperature; Large scale; Enzymatic reaction; regioselective reaction;	91.3%
With sodium hydroxide; lipase In tetrahydrofuran	89%

n-heptan1ol (111-70-6) + [(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate (13042-38-1) → isosorbide 2-acetate (13042-39-2)

Conditions	Yield
In acetone	91%

acetic anhydride (108-24-7) + Isosorbide (652-67-5) → isosorbide 2-acetate (13042-39-2) + (6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate (65940-93-4) + [(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate (13042-38-1)

Conditions	Yield
at 120 - 140℃; for 1h; Yields of byproduct given;	A 90% B n/a C n/a
With pyridine at 20℃; for 24h; Product distribution; other acylating agents;

isosorbide 2-acetate-5-mononitrate (39813-48-4) → isosorbide 2-acetate (13042-39-2)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate for 24h;	90%

acetyl chloride (75-36-5) + Isosorbide (652-67-5) → isosorbide 2-acetate (13042-39-2)

Conditions	Yield
Stage #1: Isosorbide With methylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: acetyl chloride In tetrahydrofuran at 0℃; for 2h; Reagent/catalyst; Temperature;	78%

acetic anhydride (108-24-7) + Isosorbide (652-67-5) → isosorbide 2-acetate (13042-39-2)

Conditions	Yield
at 120 - 140℃; for 1h;	70%
With potassium hydroxide 1.) 120-140 deg C, 1 h, 2.) reflux; Yield given. Multistep reaction;

acetic acid (64-19-7) + Isosorbide (652-67-5) → isosorbide 2-acetate (13042-39-2) + (6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate (65940-93-4) + [(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate (13042-38-1)

Conditions	Yield
Stage #1: acetic acid; Isosorbide In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 3h; Inert atmosphere;	A 64% B n/a C n/a
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;	A 60% B n/a C n/a
hydrogenchloride In 1,4-dioxane at 20 - 160℃; for 0.366667h; Microwave irradiation;

D-sorbitol (50-70-4) + acetic acid (64-19-7) → isosorbide 2-acetate (13042-39-2) + (6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate (65940-93-4) + [(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate (13042-38-1)

Conditions	Yield
With phosphotungstic acid In toluene at 170℃; for 6h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube; Overall yield = 83 percent;	A 13% B 9% C 61%

acetic anhydride (108-24-7) + Isosorbide (652-67-5) → isosorbide 2-acetate (13042-39-2) + (6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate (65940-93-4)

Conditions	Yield
at 120℃; for 1h;	A 13.5% B 22.5%
With scandium tris(trifluoromethanesulfonate) at 20℃; for 0.166667h; Reagent/catalyst; Overall yield = 54%;	A n/a B n/a

D-sorbitol (50-70-4) + ethyl acetate (141-78-6) → isosorbide 2-acetate (13042-39-2) + Isosorbide (652-67-5)

Conditions	Yield
With calcium sulfate In 1,4-dioxane at 78 - 84℃; for 120h; Heating;	A 21% B n/a

acetic acid (64-19-7) + Isosorbide (652-67-5) → isosorbide 2-acetate (13042-39-2) + [(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate (13042-38-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2.5h; Ambient temperature;	A 68 % Chromat. B 12 % Chromat.

vinyl acetate (108-05-4) + Isosorbide (652-67-5) → isosorbide 2-acetate (13042-39-2) + (6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate (65940-93-4)

Conditions	Yield
With Candida antarctica B In chloroform for 120h; Product distribution; Further Variations:; Reagents; Acetylation;

potassium hydrogensulfate (7646-93-7) + Isosorbide (652-67-5) → isosorbide 2-acetate (13042-39-2)

Conditions	Yield
In diethyl ether; diethylene glycol dimethyl ether; water; acetic acid; toluene

Isosorbide (652-67-5) → isosorbide 2-acetate (13042-39-2)

Conditions	Yield
With sodium acetate; acetic anhydride
Multi-step reaction with 2 steps 1: Amberlite® IR-120 / 2 h / 80 °C 2: methylmagnesium chloride / tetrahydrofuran / 8 h / Reflux View Scheme

D-sorbitol (50-70-4) + acetic acid (64-19-7) → isosorbide 2-acetate (13042-39-2) + (6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate (65940-93-4) + Isosorbide (652-67-5) + [(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate (13042-38-1)

Conditions	Yield
Amberlyst 35 resin at 85℃;

acetic acid (64-19-7) + Isosorbide (652-67-5) → D-sorbitol (50-70-4) + isosorbide 2-acetate (13042-39-2) + (6S,3R,3aR,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl acetate (65940-93-4) + [(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate (13042-38-1)

Conditions	Yield
Amberlyst 35 resin at 85℃;

acetic acid (64-19-7) + Isosorbide (652-67-5) → isosorbide 2-acetate (13042-39-2)

Conditions	Yield
Stage #1: acetic acid; Isosorbide With toluene-4-sulfonic acid In toluene Heating; Stage #2: With potassium hydroxide under 0.1 Torr;

isosorbide mononitrate (16106-20-0, 16908-90-0, 16908-91-1, 35993-37-4, 38709-03-4, 114718-64-8, 127001-76-7, 16051-77-7) → isosorbide 2-acetate (13042-39-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 3 h 2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h View Scheme

D-sorbitol (50-70-4) + acetic anhydride (108-24-7) → isosorbide 2-acetate (13042-39-2)

Conditions	Yield
With phosphotungstic acid; acetic acid at 150℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube;

isosorbide 2-acetate (13042-39-2) + benzenesulfonyl chloride (98-09-9) → (1R,4S,5R,8R)-4-acetoxy-8-benzenesulfonyloxy-2,6-dioxabicyclo<3.3.0>octane

Conditions	Yield
With pyridine at 0℃;	96%

isosorbide 2-acetate (13042-39-2) → 2(5)-O-acetyl-5(2)-chloro-5(2)-deoxy-1,4:3,6-dianhydro-L-iditol (73952-86-0)

Conditions	Yield
With pyridine; thionyl chloride at 0 - 100℃;	96%
Multi-step reaction with 2 steps 1: 83 percent 2: 73 percent / pyridine hydrochloride / pyridine / 48 h / Heating View Scheme

isosorbide 2-acetate (13042-39-2) + 3-(bromomethyl)-2-oxido-4-phenyl-1,2,5-oxadiazole (169614-78-2) → (2-O-acetyl-1,4:3,6-dianhydro-5-O-[(2-oxido-4-phenyl-1,2,5-oxadiazol-3-yl)methyl]-D-glucitol)

Conditions	Yield
With silver(l) oxide In dichloromethane for 72h; Reflux; Darkness;	96%

isosorbide 2-acetate (13042-39-2) + allyl bromide (106-95-6) → 2-O-acetyl-5-O-allyl-1,4:3,6-dianhydro-D-glucitol (162306-05-0)

Conditions	Yield
With calcium sulfate; silver(l) oxide for 48h; Ambient temperature;	93%
With calcium sulfate; silver(l) oxide at 20℃; for 48h;

isosorbide 2-acetate (13042-39-2) + methyl iodide (74-88-4) → 2-O-acetyl-1,4:3,6-dianhydro-5-O-methyl-D-glucitol (162306-07-2)

Conditions	Yield
With calcium sulfate; silver(l) oxide for 48h; Ambient temperature;	92%
With calcium sulfate; silver(l) oxide at 20℃; for 48h;	92%

trifluoromethylsulfonic anhydride (358-23-6) + isosorbide 2-acetate (13042-39-2) → (3S,6R)-6-(((trifluoromethyl)sulfonyl)oxy)hexahydrofuro[3,2-b]furan-3-yl acetate

Conditions	Yield
With pyridine In dichloromethane at -10 - 0℃; for 4h; Inert atmosphere;	90.1%

isosorbide 2-acetate (13042-39-2) + p-toluenesulfonyl chloride (98-59-9) → (3S,3aR,6R,6aS)-6-{[(4-methylphenyl)sulfonyl]oxy}hexahydrofuro[3,2-b]furan-3-yl acetate (111443-17-5)

Conditions	Yield
With pyridine at 20℃; for 8h;	86%

isosorbide 2-acetate (13042-39-2) → isosorbide 2-acetate-5-mononitrate (39813-48-4)

Conditions	Yield
With nitric acid; acetic anhydride In dichloromethane; water	85%
With nitric acid; acetic anhydride at 0℃;
With nitric acid; acetic acid
With nitric acid; acetic anhydride at 20℃; for 2h; Temperature; Inert atmosphere; Sealed tube;	28 %Chromat.

benzyl bromide (100-39-0) + isosorbide 2-acetate (13042-39-2) → 2-O-acetyl-1,4:3,6-dianhydro-5-O-benzyl-D-glucitol (162426-81-5)

Conditions	Yield
With calcium sulfate; silver(l) oxide for 48h; Ambient temperature;	85%
With sodium hydride In tetrahydrofuran at 25 - 60℃; for 5h;

(3-(bromomethyl)-4-(4-nitrophenyl)-2-oxido-1,2,5-oxadiazole) + isosorbide 2-acetate (13042-39-2) → (1,4:3,6-dianhydro-5-O-[4-(4-nitrophenyl)-2-oxido-1,2,5-oxadiazol-3-yl]methyl-D-glucitol)

Conditions	Yield
With silver(l) oxide In dichloromethane for 72h; Reflux; Darkness;	85%

isosorbide 2-acetate (13042-39-2) → 2-O-acetyl-1,4:3,6-dianhydro-5-O-(methylsulfonyl)-D-glucitol (73938-79-1, 73952-87-1, 134237-15-3)

Conditions	Yield
	83%

1-iodo-butane (542-69-8) + isosorbide 2-acetate (13042-39-2) → 2-O-acetyl-1,4:3,6-dianhydro-5-O-butyl-D-glucitol (162306-06-1)

Conditions	Yield
With calcium sulfate; silver(l) oxide In tetrahydrofuran Heating;	80%

isosorbide 2-acetate (13042-39-2) → 1,4-3,6-dianhydro-5-keto-D-glucitol-2-acetate

Conditions	Yield
With dipyridinium dichromate; acetic anhydride In dichloromethane at 50℃; for 4h;	64%

pyridine-3-carbonyl chloride hydrochloride (20260-53-1) + isosorbide 2-acetate (13042-39-2) → isosorbide 2-acetate-5-nicotinate

Conditions	Yield
With dmap; triethylamine In dichloromethane for 24h;	64%

isosorbide 2-acetate (13042-39-2) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-O-acetyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)isosorbide

Conditions	Yield
With silver(l) oxide In dichloromethane at 20℃; for 36h;	53%

isosorbide 2-acetate (13042-39-2) + 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose (3068-31-3) → 2-O-acetyl-5-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)isosorbide

Conditions	Yield
With silver(l) oxide In dichloromethane at 20℃; for 36h;	48%

isosorbide 2-acetate (13042-39-2) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 2-O-acetyl-5-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)isosorbide

Conditions	Yield
With silver(l) oxide In dichloromethane at 20℃;	34%

isosorbide 2-acetate (13042-39-2) → (3S,3aR,6R,6aR)-3-(allyloxy)-6-methoxy-hexahydrofuro[3,2-b]furan (936828-56-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / Ag2O; CaSO4 / 48 h / 20 °C 2: 86 percent / KOH / ethanol / 0.5 h / 50 °C 3: 98 percent / Ag2O; CaSO4 / 48 h / 20 °C View Scheme

Upstream product

• 50-70-4 D-sorbitol 
• 141-78-6 ethyl acetate 
• 108-24-7 acetic anhydride 
• 652-67-5 Isosorbide 
• 64-19-7 acetic acid 
• 13042-38-1 [(3S,3aR,6R,6aR)-6-acetoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl] acetate 
• 75-36-5 acetyl chloride 
• 39813-48-4 isosorbide 2-acetate-5-mononitrate 
• 16106-20-0 isosorbide mononitrate 
• 7646-93-7 potassium hydrogensulfate 
• 111-70-6 n-heptan1ol 
• 108-05-4 vinyl acetate 
• 108-22-5 Isopropenyl acetate 
• 1214839-99-2 (3R,6S)-hexahydrofuro[3,2-b]furan-3,6-diol 

Downstream Products

• 16106-20-0 isosorbide mononitrate 
• 153062-03-4 (1R,4S,5R,8R)-8-benzyloxy-4-toluenesulfonyloxy-2,6-dioxabicyclo<3.3.0>octane 
• 72631-67-5 (1R,4S,5R,8R)-8-benzyloxy-2,6-dioxabicyclo<3.3.0>octan-4-ol 
• 101128-84-1 (3R,3aS,6S,6aR)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate 
• 101222-62-2 (3R,3aS,6S,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate 
• 853016-84-9 N-benzyl-N-[(3R,3aR,6R,6aS)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl]-N-methylamine 
• 853016-76-9 N-benzyl-N-[(3S,3aR,6S,6aS)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl]-N-methylamine 
• 853016-81-6 N-benzyl-N-[(3R,3aR,6R,6aS)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl]amine 
• 853016-75-8 N-benzyl-N-[(3S,3aR,6S,6aS)-6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-yl]amine 
• 111443-17-5 (3S,3aR,6R,6aS)-6-{[(4-methylphenyl)sulfonyl]oxy}hexahydrofuro[3,2-b]furan-3-yl acetate 
• 162426-81-5 2-O-acetyl-1,4:3,6-dianhydro-5-O-benzyl-D-glucitol 

Related news

Biocatalysis in organic solvents: a process for multigram synthesis of 1,4:3,6-Dianhydro-D-glucitol 2-acetate (cas 13042-39-2) and its isomeric 5-acetate using immobilized lipase from P seudomonas sp.09/08/2019

1,4:3,6-dianhydro-D-glucitol 2-acetate (4) and its isomeric 5-actetate (2) derivatives has been prepared on multigram scale using immobilized Pseudomonas sp. lipase mediated acylation/deacylation reactions in organic solvents. The acylation of 1,4:3,6-dianhydro-D-glucitol (1) occurred in ethyl a...detailed

Relevant articles and documents

Volatile short-chain amphiphiles derived from isosorbide: Hydrotropic properties of esters vs. ethers

Two series of short-chain isosorbide monoalkanoates, differing from the free hydroxyl position, were synthesized and evaluated as volatile non-ionic hydrotropes, also known as solvo-surfactants . Their aqueous solubilities, solubilizing efficiencies and volatilities were evaluated and compared to the corresponding 5-O-alkylisosorbides. Whatever the acylation position (5-O- or 2-O-), isosorbide monoalkanoates are poorly water-soluble for acyl chains longer than four carbons, whereas 5-O-alkylisosorbides are completely miscible with water up to a pentyl chain, which seems to indicate that an ether link brings more hydrophilicity than an ester bond for these types of molecules. The shorter isosorbide monoalkanoates are completely miscible with water and the butanoates are particularly efficient in terms of aqueous solubilization of hydrophobic compounds. In addition, all hydrotropes exhibit some volatility albeit being non-VOC and contrarily to their ethers homologues, isosorbide alkanoates are easily hydrolysed in basic medium, which suggests a good biodegradability.

Method for synthesizing isohexitol ester

The invention discloses a method for synthesizing isohexitol ester, which is characterized in that a material containing hexitol and an esterifying agent is contacted with a solid acid catalyst in the presence of an aprotic solvent, and the isohexitol ester is obtained through one-pot one-step reaction. The method is especially suitable for the reaction of directly synthesizing the isohexitol ester, especially isosorbide ester, from hexitol, especially sorbitol, the total yield of the obtained isohexitol ester is 80% or above, and the yield of the isosorbide dicarboxylate reaches 60% or above.

Selective Methylmagnesium Chloride Mediated Acetylations of Isosorbide: A Route to Powerful Nitric Oxide Donor Furoxans

Isosorbide was functionalized with furoxan for the first time to give adducts that release nitric oxide up to 7.5 times faster than the commercial vasodilator, isosorbide-5-mononitrate (Is5N). The synthesis was facilitated by MeMgCl-mediated selective acetylation of isosorbide or selective deacetylation of isosorbide-2,5-diacetate, which was rationalized in terms of a more stable 5-alkoxide magnesium salt using DFT. Isosorbide-furoxans are safer to handle than Is5N due to greater thermal stability.