1,6:2,3-Dianhydro-4-O-allyl-beta-D-mannopyranose

Base Information

• Chemical Name: 1,6:2,3-Dianhydro-4-O-allyl-beta-D-mannopyranose
• CAS No.: 91510-63-3
• Molecular Formula: C9H12 O4
• Molecular Weight: 184.18918
• DSSTox Substance ID: DTXSID401215303
• Nikkaji Number: J940.163F
• Mol file: 91510-63-3.mol

Synonyms:SCHEMBL17061076;DTXSID401215303;91510-63-3;1,6:2,3-Dianhydro-4-O-allyl-beta-D-mannopyranose;1,6:2,3-Dianhydro-4-O-2-propen-1-yl-beta-D-mannopyranose

Chemical Property of 1,6:2,3-Dianhydro-4-O-allyl-beta-D-mannopyranose

Chemical Property:

• PSA: 40.22000
• LogP: 0.08010
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 184.07355886
• Heavy Atom Count: 13
• Complexity: 230

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCOC1C2COC(O2)C3C1O3
• Isomeric SMILES: C=CCO[C@@H]1[C@H]2CO[C@H](O2)[C@@H]3[C@H]1O3

Technology Process of 1,6:2,3-Dianhydro-4-O-allyl-beta-D-mannopyranose

There total 8 articles about 1,6:2,3-Dianhydro-4-O-allyl-beta-D-mannopyranose 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: 95.0%

1,6:2,3-dianhydro-β-D-mannopyranose (3868-03-9) + allyl bromide (106-95-6) → 4-O-Allyl-1,6:2,3-dianhydro-β-D-mannopyranose (91510-63-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(01)01354-5

Reference yield: 72.0%

4-O-Allyl-1,6-anhydro-2-O-tosyl-β-D-glucopyranose (39697-97-7) → 4-O-Allyl-1,6:2,3-dianhydro-β-D-mannopyranose (91510-63-3)

Guidance literature:

With sodium methylate; In dichloromethane; at -15 ℃; for 2h;

DOI:10.1002/jlac.198619860609

Reference yield: 70.0%

allyl bromide (106-95-6) + D-glucal (13265-84-4) → 4-O-Allyl-1,6:2,3-dianhydro-β-D-mannopyranose (91510-63-3)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(01)01354-5

upstream raw materials:

4-O-Allyl-1,6-anhydro-2-O-tosyl-β-D-glucopyranose

allyl alcohol

levoglucosan

1,6:2,3-dianhydro-β-D-mannopyranose

Downstream raw materials:

(1R,2S,3R,4R,5R)-2-Allyloxy-4-azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

1,6-anhydro-3-O-benzyl-2,4-dideoxy-2-C-methyl-4-methylene-β-D-xylohexopyranose

1,6-anhydro-3-O-benzyl-2-desoxy-2,4-di-C-methyl-β-D-glucopyranose

1,6-anhydro-2-desoxy-2-C-methyl-3-O-benzyl-β-D-glucopyranose