A synthetic intermediate used in glycosylation reactions
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3,4,6-Tri-O-benzyl-β-D-Mannopyranose 1,2-(methyl orthoacetate)

Item No. 16405

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,2-O-(1-methoxyethylidene)-3,4,6-tris-O-(phenylmethyl)-β-D-mannopyranose
CAS Number
16697-49-7
Molecular Formula
C30H34O7
Formula Weight
506.6
Purity
≥85%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMF:PBS(pH7.2) (1:2): 0.3 mg/mlDMSO: 10 mg/mlEthanol: 5 mg/ml
SMILES
COC1(C)O[C@]2([H])O[C@H](COCC3=CC=CC=C3)[C@@H](OCC4=CC=CC=C4)[C@H](OCC5=CC=CC=C5)[C@]2([H])O1
InChi Code
InChI=1S/C30H34O7/c1-30(31-2)36-28-27(34-20-24-16-10-5-11-17-24)26(33-19-23-14-8-4-9-15-23)25(35-29(28)37-30)21-32-18-22-12-6-3-7-13-22/h3-17,25-29H,18-21H2,1-2H3/t25-,26-,27+,28+,29+,30?/m1/s1
InChi Key
SCDVHQXHQOSKCS-LGPOITBMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 mg

    $36

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    250 mg

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    500 mg

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    1 g

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    Product Description

    3,4,6-Tri-O-benzyl-β-D-mannopyranose 1,2-(methyl orthoacetate) is a synthetic intermediate used in glycosylation reactions.1,2 Typically, the methyl orthoester protecting group is first removed by mild acid hydrolysis, producing a glycosyl donor. Removal of the O-benzyl protecting groups is performed late in the synthesis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Marino-Albernas, J.R., Bittman, R., Peters, A., et al. Synthesis and growth inhibitory properties of glycosides of 1-O-hexadecyl-2-O-methyl-sn-glycerol, analogs of the antitumor ether lipid ET-18-OCH3 (edelfosine). J. Med. Chem. 39(17), 3241-3247 (1996).

    2. Chakraborty, N., and d'Alarcao, M. An anionic inositol phosphate glycan pseudotetrasaccharide exhibits high insulin-mimetic activity in rat adipocytes. Bioorg. Med. Chem. 13(24), 6732-6741 (2005).