Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside
- Product Name
- Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside
- CAS No.
- 64363-77-5
- Chemical Name
- Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside
- Synonyms
- Methyl-2,3,4-tri-O-benzyl-a/b-D-ribopyranoside;Methyl-2,3,4-tri-O-benzyl-α/β-D-ribopyranoside;Methyl 2,3,5-tris-O-(phenylmethyl)-D-Ribofuranoside;D-Ribofuranoside, Methyl 2,3,5-tris-O-(phenylMethyl)-;(2R,3R,4R)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran;Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside,Methyl 2,3,5-tris-O-(phenylmethyl)-D-Ribofuranoside
- CBNumber
- CB12603552
- Molecular Formula
- C27H30O5
- Formula Weight
- 434.52
- MOL File
- 64363-77-5.mol
Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside Property
- Boiling point:
- 235 °C(Press: 0.3 Torr)
- Density
- 1.17±0.1 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 9861AB
- Product name
- (2R,3R,4R)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran
- Packaging
- 100mg
- Price
- $103
- Updated
- 2021/12/16
- Product number
- 9861AB
- Product name
- (2R,3R,4R)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran
- Packaging
- 250mg
- Price
- $122
- Updated
- 2021/12/16
- Product number
- MM31847
- Product name
- Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside
- Packaging
- 1g
- Price
- $185
- Updated
- 2021/12/16
- Product number
- 9861AB
- Product name
- (2R,3R,4R)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran
- Packaging
- 1g
- Price
- $220
- Updated
- 2021/12/16
- Product number
- CRB0005197
- Product name
- (2R,3R,4R)-3,4-BIS(BENZYLOXY)-2-((BENZYLOXY)METHYL)-5-METHOXYTETRAHYDROFURAN
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $503.33
- Updated
- 2021/12/16
Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside Chemical Properties,Usage,Production
Uses
Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1].
Synthesis
1824-96-0
100-39-0
64363-77-5
12 g (73.1 mmol) of methyl ALPHA-D-xylofuranoside was placed in a 250 mL aubergine flask, 160 mL of analytically pure DMF was added, and 17 g of NaH (60% dispersed in mineral oil) was added in batches under ice bath cooling. Subsequently, 38 mL of benzyl bromide was slowly added dropwise, and after completion of the dropwise addition, the reaction was gradually warmed to room temperature and stirred overnight. The reaction was monitored by TLC. Upon completion of the reaction, the reaction was quenched by careful addition of methanol and then the reaction mixture was extracted with ethyl acetate (EA). The organic phase was washed three times with water, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (eluent: petroleum ether/ethyl acetate = 15:1 to 9:1) to afford the target compound (2R,4S)-3,4-bis(benzyloxy)-2-((phenylmethoxy)methyl)-5-methoxytetrahydrofuran (28.6 g, 65.8 mmol, 90% yield).
References
[1] Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88. DOI:10.2174/138161212801227005
Methyl 2,3,5-tri-O-benzyl-D-ribofuranoside Preparation Products And Raw materials
Raw materials
Preparation Products
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