(1s,4s,5r)-6,8-Dioxabicyclo[3.2.1]octan-4-ol

Base Information

• Chemical Name: (1s,4s,5r)-6,8-Dioxabicyclo[3.2.1]octan-4-ol
• CAS No.: 39682-49-0
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.144
• Nikkaji Number: J596.598E
• Mol file: 39682-49-0.mol

Synonyms:(1s,4s,5r)-6,8-dioxabicyclo[3.2.1]octan-4-ol;39682-49-0;1,6-Anhydro-3,4-dideoxy-beta-D-threo-hexopyranose;IJPZEVCAPJUVHC-HCWXCVPCSA-;AT22560;InChI=1/C6H10O3/c7-5-2-1-4-3-8-6(5)9-4/h4-7H,1-3H2/t4-,5-,6+/m0/s1;89734-48-5

Chemical Property of (1s,4s,5r)-6,8-Dioxabicyclo[3.2.1]octan-4-ol

Chemical Property:

• Boiling Point: 249.8±20.0 °C(Predicted)
• PKA: 14.90±0.20(Predicted)
• Density: 1.275±0.06 g/cm3(Predicted)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 115

Purity/Quality:

99% ^*data from raw suppliers

1,6-Anhydro-3,4-dideoxy-beta-D-threo-hexopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(C2OCC1O2)O
• Isomeric SMILES: C1C[C@@H]([C@@H]2OC[C@H]1O2)O

Technology Process of (1s,4s,5r)-6,8-Dioxabicyclo[3.2.1]octan-4-ol

There total 12 articles about (1s,4s,5r)-6,8-Dioxabicyclo[3.2.1]octan-4-ol 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: 99.0%

1,6-anhydro-3,4-dideoxy-β-D-glycero-hexopyranos-2-ulose (53716-82-8) → 1,6-anhydro-3,4-dideoxy-D-threo-hexopyranoside and 1,6-anhydro-3,4-dideoxy-D-threo-hexopyranoside (39682-49-0)

Guidance literature:

With D-glucose; In water; at 30 ℃; for 24h; diastereoselective reaction;

DOI:10.1007/s10593-019-02415-7

Reference yield: 71.0%

1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose (50705-28-7) → 1,6-anhydro-3,4-dideoxy-D-threo-hexopyranoside and 1,6-anhydro-3,4-dideoxy-D-threo-hexopyranoside (39682-49-0) + 1,6-anhydro-3,4-dideoxy-β-D-glycero-hexopyranos-2-ulose (53716-82-8)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethyl acetate; at 20 ℃; Reagent/catalyst;

DOI:10.1016/j.mencom.2019.03.029

Reference yield: 39.0%

1,6-anhydro-2,3-dideoxy-β-D-erythro-hexopyranos-2-ulose (58238-45-2) → 1,6-anhydro-3,4-dideoxy-D-threo-hexopyranoside and 1,6-anhydro-3,4-dideoxy-D-threo-hexopyranoside (39682-49-0) + (1R,2S,4S,5R)-6,8-dioxabicyclo[3.2.1]octane-2,4-diol (29514-09-8)

Guidance literature:

With D-glucose; In water; at 30 ℃; for 24h; stereoselective reaction; Enzymatic reaction;

DOI:10.1016/j.mencom.2019.03.029

upstream raw materials:

[(1R,2S,3S,4R,5R)-3-hydroxy-4-(p-tolylsulfonyl)-6,8-dioxabicyclo[3.2.1]oct-2-yl]-4-methylbenzenesulfonic acid

levoglucosan tritosylate

levoglucosan

1,6-anhydro-3,4-dideoxy-β-D-glycero-hexopyranos-2-ulose

Downstream raw materials:

1,6-anhydro-3,4-dideoxy-β-D-glycero-hexopyranos-2-ulose