361763
2,3:5,6-Di-O-isopropylidene-α-D-mannofuranose
97%
Synonym(s):
D-Mannose diacetonide
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About This Item
Empirical Formula (Hill Notation):
C12H20O6
CAS Number:
Molecular Weight:
260.28
UNSPSC Code:
12352201
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
84382
InChI
1S/C12H20O6/c1-11(2)14-5-6(16-11)7-8-9(10(13)15-7)18-12(3,4)17-8/h6-10,13H,5H2,1-4H3/t6?,7-,8+,9?,10?/m1/s1
SMILES string
CC1(C)OC[C@@H](O1)[C@H]2OC(O)[C@@H]3OC(C)(C)O[C@@H]23
InChI key
JWWCLCNPTZHVLF-RGJLLFKYSA-N
assay
97%
form
solid
optical activity
[α]20/D +23°, c = 1 in acetone
mp
125-126 °C (dec.) (lit.)
Quality Level
Application
Protected mannose intermediate used in the syntheses of ovalicin and of the sugar core of hikizimycin.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
涉药品监管产品
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Furstner, A. et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 12, 76-76 (2006)
Shunya Takahashi et al.
The Journal of organic chemistry, 70(24), 10162-10165 (2005-11-19)
[reaction: see text] A new synthesis of epoxyketone 22 is described that is a key intermediate in Barton's synthesis of ovalicin (2), a powerful anti-angiogenetic inhibitor. The key process for the construction of 22 was ring-closing metathesis of olefins 11
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