.beta.-D-Mannopyranose, 1,6:2,3-dianhydro-4-O-(phenylmethyl)-

Base Information

• Chemical Name: .beta.-D-Mannopyranose, 1,6:2,3-dianhydro-4-O-(phenylmethyl)-
• CAS No.: 33208-47-8
• Molecular Formula: C13H14 O4
• Molecular Weight: 234.252
• Mol file: 33208-47-8.mol

Synonyms:Mannopyranose,1,6:2,3-dianhydro-4-O-benzyl-, b-D- (8CI); 3,8,9-Trioxatricyclo[4.2.1.02,4]nonane, b-D-mannopyranose deriv.;1,6:2,3-Dianhydro-4-O-(phenylmethyl)-b-D-mannopyranose; 1,6:2,3-Dianhydro-4-O-benzyl-b-D-mannopyranose

Chemical Property of .beta.-D-Mannopyranose, 1,6:2,3-dianhydro-4-O-(phenylmethyl)-

Chemical Property:

• PSA: 40.22000
• LogP: 1.09430

Purity/Quality:

99% ^*data from raw suppliers

1,6:2,3-Dianhydro-4-O-benzyl-b-D-mannopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of .beta.-D-Mannopyranose, 1,6:2,3-dianhydro-4-O-(phenylmethyl)-

There total 16 articles about .beta.-D-Mannopyranose, 1,6:2,3-dianhydro-4-O-(phenylmethyl)- 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) + benzyl bromide (100-39-0) → 4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8)

Guidance literature:

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

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

Reference yield: 85.0%

1,6-anhydro-4-O-benzyl-2-iodo-2-deoxy-β-D-glucopyranose (50767-55-0) → 4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8)

Guidance literature:

With potassium carbonate; In acetonitrile; at 60 ℃; for 2h; Inert atmosphere;

Reference yield: 85.0%

1,6-anhydro-4-O-benzyl-2-bromo-2-deoxy-β-D-glucopyranose (110046-93-0) → 4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8)

Guidance literature:

With potassium carbonate; In methanol; water; for 120h; Ambient temperature;

upstream raw materials:

1,6-anhydro-4-O-benzyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranose

1,6-anhydro-4-O-benzyl-3-O-(N-benzylcarbamoyl)-2-O-p-tolylsulfonyl-β-D-glucopyranose

1,6-anhydro-4-O-benzyl-2-bromo-2-deoxy-β-D-glucopyranose

1,6:2,3-dianhydro-β-D-mannopyranose

Downstream raw materials:

1,6-anhydro-4-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

1,6-anhydro-4-O-benzyl-2-deoxy-2-C-vinyl-β-D-glucopyranose

1,6-anhydro-4-O-benzyl-2-chloro-2-deoxy-β-D-glucopyranose

1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(2-propenyl)-β-D-glucopyranose

Refernces

• 1、 Katavic, Peter L.,Yong, Ken W.L.,Herring, Joel N.,Deseo, Myrna A.,Blanchfield, Joanne T.,Ferro, Vito,Garson, Mary J.. "Structure and stereochemistry of an anti-inflammatory anhydrosugar from the Australian marine sponge Plakinastrella clathrata and the synthesis of two analogues". . p. 8074 - 8079. Retrieved 2013/08/23.
• 2、 Hesek, Dusan,Lee, Mijoon,Zhang, Weilie,Noll, Bruce C.,Mobashery, Shahriar. "Total synthesis of n-acetylglucosamine-1,6-anhydro-n- acetylmuramylpentapeptide and evaluation of its turnover by ampd from escherichia coli". supporting information; experimental part. p. 5187 - 5193. Retrieved 2009/09/30.