4-O-Benzyl-D-glucal

Base Information

• Chemical Name: 4-O-Benzyl-D-glucal
• CAS No.: 58871-11-7
• Molecular Formula: C13H16 O4
• Molecular Weight: 236.268
• DSSTox Substance ID: DTXSID50370467
• Nikkaji Number: J1.608.712B
• Wikidata: Q82157621
• Mol file: 58871-11-7.mol

Synonyms:4-O-Benzyl-D-glucal;58871-11-7;(2R,3S,4R)-2-(hydroxymethyl)-3-phenylmethoxy-3,4-dihydro-2H-pyran-4-ol;(2R,3S,4R)-3-(benzyloxy)-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-4-ol;4-O-BENZYL-D-GLUCAL,;MFCD01863610;SCHEMBL630147;4-O-Benzyl-D-glucal, 97%;DTXSID50370467;OIWQZGBSQDJVJN-UPJWGTAASA-N;CS-0454029;1,2-Dideoxy-4-O-benzyl-D-arabino-1-hexenopyranose;W-203210

Chemical Property of 4-O-Benzyl-D-glucal

Chemical Property:

• Vapor Pressure: 1.4E-07mmHg at 25°C
• Melting Point: 99-103 °C(lit.)
• Boiling Point: 413.5 °C at 760 mmHg
• Flash Point: 203.9 °C
• PSA: 58.92000
• Density: 1.25 g/cm³
• LogP: 0.83750
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 236.10485899
• Heavy Atom Count: 17
• Complexity: 248

Purity/Quality:

99% ^*data from raw suppliers

4-O-Benzyl-D-glucal 97% ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2C(C=COC2CO)O
• Isomeric SMILES: C1=CC=C(C=C1)CO[C@H]2[C@@H](C=CO[C@@H]2CO)O

Technology Process of 4-O-Benzyl-D-glucal

There total 10 articles about 4-O-Benzyl-D-glucal 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: 90.0%

4-O-benzyl-1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose (111830-58-1) → 4-O-benzyl-D-(-)-glucal (58871-11-7)

Guidance literature:

With tetrabutyl ammonium fluoride; at 20 ℃; Cooling with ice; Inert atmosphere;

Reference yield: 72.0%

benzyl bromide (100-39-0) + D-glucal triacetate (2873-29-2) → 4-O-benzyl-D-(-)-glucal (58871-11-7)

Guidance literature:

D-glucal triacetate; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide;

With methanol; In N,N-dimethyl-formamide; for 0.5h;

Reference yield:

4-O-benzyl-6-O-tert-butyldimethylsilyl-D-(-)-glucal (137792-62-2) → 4-O-benzyl-D-(-)-glucal (58871-11-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1021/ol991176c

upstream raw materials:

4-O-benzyl-6-O-tert-butyldimethylsilyl-D-(-)-glucal

4-O-benzyl-1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose

benzyl bromide

1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose

Downstream raw materials:

4-O-benzyl-1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose

4-O-benzyl-6-O-tert-butyldimethylsilyl-D-(-)-glucal