1,3,4,6-Tetra-O-acetyl-beta-d-mannopyranose

Base Information

• Chemical Name: 1,3,4,6-Tetra-O-acetyl-beta-d-mannopyranose
• CAS No.: 18968-05-3
• Molecular Formula: C14H20O10
• Molecular Weight: 348.307
• Hs Code.: 29400090
• European Community (EC) Number: 606-186-5
• DSSTox Substance ID: DTXSID80428485
• Nikkaji Number: J82.814I
• Wikidata: Q82241318
• Mol file: 18968-05-3.mol

Synonyms:18968-05-3;1,3,4,6-Tetra-O-acetyl-beta-d-mannopyranose;(2S,3S,4R,5R,6R)-6-(Acetoxymethyl)-3-hydroxytetrahydro-2H-pyran-2,4,5-triyl triacetate;1,3,4,6-Tetra-o-acetyl-b-D-mannopyranose;[(2R,3R,4R,5S,6S)-3,4,6-triacetyloxy-5-hydroxyoxan-2-yl]methyl acetate;b-D-Mannopyranose,1,3,4,6-tetraacetate;MFCD00012354;1,3,4,6-Tetra-O-acetylhexopyranose #;1,3,4,6-Tetra-O-acetyl-?-D-mannopyranose;SCHEMBL3190848;AMY5222;DTXSID80428485;AKOS022176185;s11188;DS-12583;1,3,4,6-tetra-o-acetyl--d-mannopyranose;beta-D-Mannopyranose 1,3,4,6-tetraacetate;T1459;1,3,4,6-Tetra-O-acetyl-$b-D-mannopyranose;beta-D-Mannopyranose, 1,3,4,6-tetraacetate;beta-D-Mannopyranose 1,3,4,6-tetra-O-acetate;1,3,4,6-Tetra-O-acetyl- beta -D-mannopyranose;A813346;J-640427;J-800481;W-201695;1,3,4,6-Tetra-O-acetyl-beta-D-mannopyranose, 98%;(2S,3S,4R,5R,6R)-6-(Acetoxymethyl)-3-hydroxytetrahydro-2H-pyran-2,4,5-triyltriacetate

Chemical Property of 1,3,4,6-Tetra-O-acetyl-beta-d-mannopyranose

Chemical Property:

• Vapor Pressure: 0.329mmHg at 25°C
• Melting Point: 160-161 °C(lit.)
• Refractive Index: -22.5 ° (C=1.4, CHCl3)
• Boiling Point: 425.537 °C at 760 mmHg
• PKA: 12.22±0.70(Predicted)
• Flash Point: 148.725 °C
• Density: 1.339 g/cm³
• Storage Temp.: Refrigerator
• Solubility.: very faint turbidity in Chloroform
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 348.10564683
• Heavy Atom Count: 24
• Complexity: 502

Purity/Quality:

98% ^*data from raw suppliers

1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)O)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)OC(=O)C)O)OC(=O)C)OC(=O)C
• Uses: 1,3,4,6-Tetra-o-acetyl-beta-d-mannopyranose is an intermediate in the preparation of precursors of 2-[18F]fluoro-2-deoxy-D-glucose for diagnostic use in positron emission tomography. An intermediate in the preparation of precursors of 2-[18F]fluoro-2-deoxy-D-glucose for diagnostic use in positron emission tomography.

Technology Process of 1,3,4,6-Tetra-O-acetyl-beta-d-mannopyranose

There total 22 articles about 1,3,4,6-Tetra-O-acetyl-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: 45.0%

3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside (28140-37-6) → 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose (18968-05-3)

Guidance literature:

With hydrogenchloride; In water; acetone; at 18 - 20 ℃; for 0.0833333h;

DOI:10.1016/j.bmc.2018.02.031

Reference yield: 29.0%

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0) → 2,3,4,6-tetra-O-acetyl-β-D-mannopyranose (57884-82-9) + 2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (22860-22-6) + 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose (18968-05-3)

Guidance literature:

With trifluoroacetic acid; In acetonitrile; at 0 ℃; for 3h; Yields of byproduct given;

Reference yield: 19.0%

1,3,4,6-Tetra-O-acetyl-β-D-arabino-hexopyranos-2-ulose monohydrate (73322-37-9) → 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose (18968-05-3)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethyl acetate; for 48h;

upstream raw materials:

O³,O⁴,O⁶-triacetyl-β-D-mannopyranosyl chloride

acetobromomannose

D-Mannose

acetic anhydride

Downstream raw materials:

1,3,4,6-tetra-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-β-D-mannopyranose

1,3,4,6-tetra-O-acetyl-2-O-benzoyl-β-D-mannopyranose

1,3,4,6-Tetra-O-acetyl-2-O-(diphenoxyphosphoryl)-β-D-mannopyranose

2-O-(6-O-benzyl-2,3,4-trideoxy-α-D-glycero-hex-2-enopyranosyl)-1,3,4,6-tetra-O-acetyl-β-D-mannopyranose

Refernces

• 1、 -. "Disulfide dimannose-gold nanoprobe as well as preparation method and application thereof". Paragraph 0030-0033. . Retrieved 2021/03/05.
• 2、 -. "A process for the purification of three fluorine mannose intermediate". Paragraph 0029. . Retrieved 2017/03/17.