3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxy-2-methylene-1-α-methyl-D-ribofuranose

Base Information

Chemical Name:3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxy-2-methylene-1-α-methyl-D-ribofuranose
CAS No.:229469-31-2
Molecular Formula:C₂₀H₃₂O₄Si
Molecular Weight:364.557
Hs Code.:

Synonyms:3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxy-2-methylene-1-α-methyl-D-ribofuranose

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Chemical Property of 3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxy-2-methylene-1-α-methyl-D-ribofuranose

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Technology Process of 3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxy-2-methylene-1-α-methyl-D-ribofuranose

There total 10 articles about 3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxy-2-methylene-1-α-methyl-D-ribofuranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

: 100-39-0
benzyl bromide

: (2R,3S,5S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methoxy-4-methylene-tetrahydro-furan-3-ol

: 229469-31-2
3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxy-2-methylene-1-α-methyl-D-ribofuranose

Guidance literature:: With sodium hydride; In tetrahydrofuran; for 4h; Ambient temperature;
DOI:10.1016/S0040-4020(99)00394-4

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 229469-31-2
3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxy-2-methylene-1-α-methyl-D-ribofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine

2: 71 percent / NaH / tetrahydrofuran / 5 h / 20 °C

With sodium hydride; In tetrahydrofuran; pyridine; 1: Substitution / 2: Substitution;
DOI:10.1080/15257779908041488

Reference yield:

: 56607-40-0
methyl D-arabinofuranoside

: 229469-31-2
3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxy-2-methylene-1-α-methyl-D-ribofuranose

Guidance literature:: Multi-step reaction with 6 steps

1: 71 percent / DMAP / pyridine / 12 h / 20 °C

2: DCC, DMSO, TFA / pyridine / 16 h / 20 °C

3: 56 percent / diethyl ether / 1 h / -10 °C

4: 100 percent / TBAF / tetrahydrofuran / 48 h / 20 °C

5: pyridine

6: 71 percent / NaH / tetrahydrofuran / 5 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; diethyl ether; 1: Substitution / 2: Oxidation / 3: Wittig reaction / 4: desilylation / 5: Substitution / 6: Substitution;
DOI:10.1080/15257779908041488