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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

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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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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