N-[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide

• ChemBase ID: 152673
• Molecular Formular: C22H25NO6
• Molecular Mass: 399.437
• Monoisotopic Mass: 399.16818753
• SMILES: CC(=O)N[C@@H]1[C@H]([C@H]2[C@@H](COC(O2)c2ccccc2)O[C@@H]1OCc1ccccc1)O
• Canonical SMILES: CC(=O)N[C@H]1[C@@H](OCc2ccccc2)O[C@H]2[C@H]([C@@H]1O)OC(OC2)c1ccccc1
• InChI: InChI=1S/C22H25NO6/c1-14(24)23-18-19(25)20-17(13-27-21(29-20)16-10-6-3-7-11-16)28-22(18)26-12-15-8-4-2-5-9-15/h2-11,17-22,25H,12-13H2,1H3,(H,23,24)/t17-,18-,19-,20-,21?,22+/m1/s1
• InChIKey: NXGXFAKJUWEFEC-NVZUTRPHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• IUPAC Traditional name: N-[(4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• Synonyms: Benzyl-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside; Phenylmethyl 2-(Acetylamino)-2-deoxy-4,6-O-(phenylmethylene)-α-D-glucopyranoside; Benzyl 2-Acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside; 苄基-2-乙酰氨基-4,6-O-苯亚甲基-2-脱氧-α-D-吡喃葡萄糖苷

Database IDs

• CAS Number: 13343-63-0
• MDL Number: MFCD00143679
• Beilstein Number: 55951
• PubChem SID: 162246816; 24848015
• PubChem CID: 2735220

CALCULATED PROPERTIES

• Acid pKa: 12.454627
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.3121042
• LogD (pH = 7.4): 2.3121011
• Log P: 2.3121045
• Molar Refractivity: 103.2721 cm^3
• Polarizability: 41.49513 Å^3
• Polar Surface Area: 86.25 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 205-208°C (dec.); 256-261 °C (dec.)
• Optical Rotation: [α]20/D +115±3°, c = 1% in pyridine

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (sum of enantiomers, HPLC)
• Empirical Formula (Hill Notation): C22H25NO6

DETAILS

Sigma Aldrich - 13145

Other Notes
Carbohydrate building block; used for the synthesis of N-acetyl muramic acid and similar compounds;1,2 preparation of derivatives of 2,3-diamino-2,3-dideoxy-glucopyranoside.3
Packaging
5 g in glass bottle

Toronto Research Chemicals - B211000

A useful synthetic intermediate for carbohydrate and oligosaccharide synthesis.