methyl 3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside

Base Information

Chemical Name:methyl 3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside
CAS No.:260434-52-4
Molecular Formula:C₃₇H₄₄O₈SSi
Molecular Weight:676.903
Hs Code.:

Synonyms:methyl 3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside

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Chemical Property of methyl 3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside

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Technology Process of methyl 3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside

There total 10 articles about methyl 3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside 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: 67.0%

: 260434-51-3
methyl 2,3-O-benzylidene-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside

: methyl 2-O-benzyl-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside

: 260434-52-4
methyl 3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside

Guidance literature:: With titanium tetrachloride; sodium cyanoborohydride; In acetonitrile; at 20 ℃;
DOI:10.1016/S0040-4039(99)01998-X

Reference yield:

: 55797-67-6
((3aS,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4,4-diyl)dimethanol

: 260434-52-4
methyl 3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / Et₃N / CH₂Cl₂ / 13 h / 20 °C

2: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 17 h / 20 °C

3: 77 percent / TFA / tetrahydrofuran; H₂O / 0.33 h / 20 °C

4: 100 percent / ZnCl₂ / 2 h / 20 °C

5: 9 percent / DIBAH / CH₂Cl₂ / 6 h / 0 - 20 °C

With dmap; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid; zinc(II) chloride; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/S0040-4020(02)00226-0

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 260434-52-4
methyl 3-O-benzyl-5-O-(tert-butyldiphenylsilyl)-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / Et₃N / CH₂Cl₂ / 13 h / 20 °C

2: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 17 h / 20 °C

3: 77 percent / TFA / tetrahydrofuran; H₂O / 0.33 h / 20 °C

4: 100 percent / ZnCl₂ / 2 h / 20 °C

5: 9 percent / DIBAH / CH₂Cl₂ / 6 h / 0 - 20 °C

With dmap; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid; zinc(II) chloride; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/S0040-4020(02)00226-0