6-O-Benzyl-D-glucal

Base Information

• Chemical Name: 6-O-Benzyl-D-glucal
• CAS No.: 165524-85-6
• Molecular Formula: C13H16O4
• Molecular Weight: 236.268
• DSSTox Substance ID: DTXSID10370468
• Nikkaji Number: J2.876.955E
• Wikidata: Q82157623
• Mol file: 165524-85-6.mol

Synonyms:6-O-Benzyl-D-glucal;165524-85-6;6-O-Benzylglucal;(2R,3S,4R)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3,4-diol;6-O-BENZYL-D-GLUCAL,;D-arabino-Hex-1-enitol, 1,5-anhydro-2-deoxy-6-O-(phenylmethyl)-;(2R,3S,4R)-2-((Benzyloxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol;(2R,3S,4R)-2-[(benzyloxy)methyl]-3,4-dihydro-2H-pyran-3,4-diol;SCHEMBL6929831;DTXSID10370468;W-201493;(2R,3S,4R)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyran-3,4-diol;D-Arabino-hex-1-enitol,1,5-anhydro-2-deoxy-6-O-(phenylmethyl)-

Chemical Property of 6-O-Benzyl-D-glucal

Chemical Property:

• Vapor Pressure: 1.38E-06mmHg at 25°C
• Refractive Index: 1.579
• Boiling Point: 384.1 °C at 760 mmHg
• PKA: 12.79±0.60(Predicted)
• Flash Point: 186.1 °C
• PSA: 58.92000
• Density: 1.247 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:

98%Min ^*data from raw suppliers

6-O-Benzyl-D-glucal ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C=CO2)O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H](C=CO2)O)O

Technology Process of 6-O-Benzyl-D-glucal

There total 2 articles about 6-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: 72.0%

benzyl bromide (100-39-0) + D-glucal (13265-84-4) → 6-O-(benzyl)-D-glucal (165524-85-6)

Guidance literature:

With 2-Aminoethoxydiphenylborane; silver(l) oxide; In acetonitrile; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol501711v

Reference yield:

D-glucal triacetate (2873-29-2) → 6-O-(benzyl)-D-glucal (165524-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / MeONa / methanol

2: LHMDS / dimethylformamide / -40 °C

With sodium methylate; lithium hexamethyldisilazane; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo048981b

Reference yield: 88.0%

pivaloyl chloride (3282-30-2) + 6-O-(benzyl)-D-glucal (165524-85-6) → 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxymethyl-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester (322648-74-8)

Guidance literature:

With pyridine; dmap; In dichloromethane;

DOI:10.1021/ja0022730

upstream raw materials:

benzyl bromide

D-glucal

D-glucal triacetate

Downstream raw materials:

3,4,6-tri-O-benzyl-D-glucal

3-O-Acetyl-4,6-di-O-benzyl-D-glucal

4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol

6-O-Benzyl-3-O-triethylsilylglucal

Refernces

• 1、 Balmond, Edward I.,Benito-Alifonso, David,Coe, Diane M.,Alder, Roger W.,McGarrigle, Eoghan M.,Galan, M. Carmen. "A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides". supporting information. p. 8190 - 8194. Retrieved 2014/08/18.
• 2、 Di Bussolo, Valeria,Caselli, Micaela,Pineschi, Mauro,Crotti, Paolo. "New stereoselective β-C-glycosidation by uncatalyzed 1,4-addition of organolithium reagents to a glycal-derived vinyl oxirane". . p. 2173 - 2176. Retrieved 2007/10/03.