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361763

Sigma-Aldrich

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:
14131-84-1
Molecular Weight:
260.28
Beilstein:
84382
MDL number:
MFCD00134206
UNSPSC Code:
12352201
PubChem Substance ID:
24862256
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

optical activity

[α]20/D +23°, c = 1 in acetone

mp

125-126 °C (dec.) (lit.)

SMILES string

CC1(C)OC[C@@H](O1)[C@H]2OC(O)[C@@H]3OC(C)(C)O[C@@H]23

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

InChI key

JWWCLCNPTZHVLF-RGJLLFKYSA-N

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Related Categories

Application

Protected mannose intermediate used in the syntheses of ovalicin and of the sugar core of hikizimycin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS3522
MKCF0611
MKBW5300V
MKBP4367V
MKBN3366V

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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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