(3R,6R)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol

Base Information

• Chemical Name: (3R,6R)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol
• CAS No.: 641-74-7
• Molecular Formula: C6H10O4
• Molecular Weight: 146.143
• Hs Code.: 29329990
• European Community (EC) Number: 211-374-1
• Nikkaji Number: J1.379.542H
• Mol file: 641-74-7.mol

Synonyms:1,4-3,6-dianhydro-D-mannitol;1,4-3,6-dianhydromannitol;isomannide

Chemical Property of (3R,6R)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol

Chemical Property:

• Appearance/Colour: Off White Crystals
• Vapor Pressure: 4.71E-07mmHg at 25°C
• Melting Point: 80-85 °C(lit.)
• Refractive Index: 1.562
• Boiling Point: 372.053 °C at 760 mmHg
• PKA: 13.17±0.40(Predicted)
• Flash Point: 178.8 °C
• PSA: 58.92000
• Density: 1.475 g/cm³
• LogP: -1.49420
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly), Water
• Water Solubility.: almost transparency
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 146.05790880
• Heavy Atom Count: 10
• Complexity: 122

Purity/Quality:

99.9% ^*data from raw suppliers

1-[4- ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C2C(O1)C(CO2)O)O
• Isomeric SMILES: C1[C@H](C2C(O1)[C@@H](CO2)O)O
• Uses: 1,4:3,6-Dianhydro-D-mannitol is a reagent used in the synthesis of new isomannide-based peptidomimetic as human tissue kallikrein 1 inhibitor using Ugi multicomponent reaction. It also functions as a chiral ligand for stereoselective synthesis.

Technology Process of (3R,6R)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol

There total 48 articles about (3R,6R)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(3S,3aR,6S,6aR)-6-(benzoyloxy)hexahydrofuro[3,2-b]furan-3-yl benzoate (3014-56-0,24332-64-7) → 1,4:3,6-dianhydro-L-iditol (641-74-7,652-67-5,5627-19-0,24332-71-6,28218-68-0,28948-16-5,28980-83-8,89825-36-5,124508-14-1,151380-60-8)

Guidance literature:

With potassium cyanide; sodium methylate; In methanol; at 25 ℃; for 2h;

DOI:10.1016/S0957-4166(02)00411-1

Reference yield: 60.0%

D-sorbitol (50-70-4) + carbonic acid dimethyl ester (616-38-6) → 1,4:3,6-dianhydro-D-mannitol (641-74-7) + 1,4:3,6-dianhydro-L-iditol (641-74-7,652-67-5,5627-19-0,24332-71-6,28218-68-0,28948-16-5,28980-83-8,89825-36-5,124508-14-1,151380-60-8) + isosorbide dimethyl ether (5306-85-4)

Guidance literature:

With triethylamine; In biphenyl; at 90 - 200 ℃; for 48h; under 63756.4 Torr; Reagent/catalyst; Autoclave; Inert atmosphere;

DOI:10.1002/cssc.201601382

Reference yield: 60.0%

D-sorbitol (50-70-4) + carbonic acid dimethyl ester (616-38-6) → 1,4:3,6-dianhydro-D-mannitol (641-74-7) + 1,4:3,6-dianhydro-L-iditol (641-74-7,652-67-5,5627-19-0,24332-71-6,28218-68-0,28948-16-5,28980-83-8,89825-36-5,124508-14-1,151380-60-8) + isosorbide dimethyl ether (5306-85-4)

Guidance literature:

With triethylamine; In biphenyl; at 90 - 200 ℃; for 48h; under 63756.4 Torr; Reagent/catalyst; Autoclave; Inert atmosphere;

DOI:10.1002/cssc.201601382

upstream raw materials:

mannitol

1,6-dichloro-2S,3S,4S,5S-hexanetetraol

tetrachloromethane

toluene-4-sulfonic acid

Downstream raw materials:

isomannide 2,5-acetate

2,5-,O'O-dibenzyl-1,4:3,6-dianhydro-D-mannitole

1,4:3,6-dianhydro-2,5-di-O-benzoyl-D-mannitol

(3R,3aR,6R,6aR)-3,6-bis(allyloxy)hexahydrofuro[3,2-b]furan

Refernces

• 1、 Bahé, Florian,Grand, Lucie,Cartier, Elise,Jacolot, Ma?wenn,Moebs-Sanchez, Sylvie,Portinha, Daniel,Fleury, Etienne,Popowycz, Florence. "Direct Amination of Isohexides via Borrowing Hydrogen Methodology: Regio- and Stereoselective Issues". supporting information. p. 599 - 608. Retrieved 2020/02/04.
• 2、 Engel, Rebecca V.,Niemeier, Johannes,Fink, Anja,Rose, Marcus. "Unravelling the Mechanism of the Ru/C-Catalysed Isohexide and Ether Isomerization by Hydrogen Isotope Exchange". supporting information. p. 2358 - 2363. Retrieved 2018/05/08.