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Merck
CN

943746

Methyl 3-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-α-D-glucopyranoside

≥95%

Synonym(s):

α-D-Glucopyranoside, methyl 3-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-, 6-O-[(R)-phenylmethylene]-α-D-glucopyranoside, Methyl 3-O-(phenylmethyl)-4, Methyl 3-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-α-D-glucopyranoside

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SMILES string

OC1C(OC)OC2COC(OC2C1OCC=3C=CC=CC3)C=4C=CC=CC4

InChI key

QRMYFVCKXAQEDN-UFOPBENGSA-N

InChI

1S/C21H24O6/c1-23-21-17(22)19(24-12-14-8-4-2-5-9-14)18-16(26-21)13-25-20(27-18)15-10-6-3-7-11-15/h2-11,16-22H,12-13H2,1H3/t16-,17-,18-,19-,20-,21+/m1/s1

assay

≥95%

form

solid

storage condition

protect from light

color

white to off-white

storage temp.

2-8°C

Quality Level

100

General description

This compound is a protected sugar derivative (a benzyl ether / acetal-containing sugar-like scaffold), specifically a benzyloxylated and methoxylated hexahydropyrano-dioxin ring system bearing a phenyl substituent at one position and multiple oxygen functionalities. It is used in carbohydrate chemistry or glycosylation strategies as a protected intermediate to control reactivity of hydroxyl groups and enable selective transformations.

Application

  • Carbohydrate synthesis: As a protected sugar building block or glycoside intermediate in oligo- or polysaccharide assembly.
  • Glycomimetic or glyco-analogue design: Use in medicinal chemistry to build sugar-like bioactive molecules.
  • Protecting strategy: As a masked sugar derivative for temporary protection in multistep synthesis of complex molecules.

Features and Benefits

  • Protected functional groups: The benzyloxy and acetal/dioxin moieties shield hydroxyl groups, preventing unwanted side reactions.
  • Structural rigidity & stereochemistry: The bicyclic sugar-like framework imparts defined stereochemical arrangement, helpful in stereoselective transformations.
  • Organic solubility: Protection increases lipophilicity and solubility in organic solvents, useful for organic-phase synthesis.
  • Versatility: After selective deprotection, the core scaffold can serve as donor/acceptor in glycosylations or be functionalized further.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000518136
0000518136

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