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01510

1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Name: 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-<SC>D</SC>-ribofuranose
Brand: SIAL

purum, ≥97.0% (TLC)

Synonym(s):

β-D-Ribofuranose 1-acetate 2,3,5-tribenzoate

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About This Item

Empirical Formula (Hill Notation):

C₂₈H₂₄O₉

CAS Number:

6974-32-9

Molecular Weight:

504.48

EC Number:

230-220-4

UNSPSC Code:

12352200

PubChem Substance ID:

24844890

Beilstein/REAXYS Number:

100243

MDL number:

MFCD00005357

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grade

purum

assay

≥97.0% (TLC)

optical activity

[α]20/D +44±1°, c = 0.5% in chloroform

mp

128-130 °C

SMILES string

CC(=O)O[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](OC(=O)c3ccccc3)[C@H]1OC(=O)c4ccccc4

InChI

1S/C28H24O9/c1-18(29)34-28-24(37-27(32)21-15-9-4-10-16-21)23(36-26(31)20-13-7-3-8-14-20)22(35-28)17-33-25(30)19-11-5-2-6-12-19/h2-16,22-24,28H,17H2,1H3/t22-,23-,24-,28-/m1/s1

InChI key

GCZABPLTDYVJMP-CBUXHAPBSA-N

Other Notes

Ribose derivative used for the synthesis of nucleosides; 1-cyanation with Me₃SiC

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

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M. Saneyoshi et al.

Chemical & Pharmaceutical Bulletin, 27, 2518-2518 (1979)

K. Utimoto et al.

Tetrahedron Letters, 23, 237-237 (1982)

A. Matsuda et al.

Synthesis, 748-748 (1981)

A general synthesis of N-glycosides. I. Synthesis of pyrimidine nucleosides.

U Niedballa et al.

The Journal of organic chemistry, 39(25), 3654-3660 (1974-12-13)

The use of iodotrimethylsilane in nucleosidation procedure.

Z Tocik et al.

Nucleic acids research, 8(20), 4755-4761 (1980-10-24)

1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (I) was reacted with iodotrimethylsilane (II) and the product, the glycosyl iodide, was coupled with silylated uracil to afford 1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)uracil (III; 89%), with silyated cytosine to afford, on subsequent acetylation, 1-(2,3,5-tri-O-benzoyl-beta-0D-ribofuranosyl)-4-acetamido-2-(1H)-pyrimidinone (IVb; 81%), and with chloromercuri-N-benzoyl-adenine to afford Va

Global Trade Item Number

SKU	GTIN
C105805-25G	04061833460627
PHR2898-3X1.2ML	04065266458633
8416200250	04022536884653
8416200050	04022536647005
1154605-2X1ML	04061837842696
C105805-100G	04061833460610
C105805-5G	04061833460634

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