methyl 5-O-(tert-butyldiphenylsilyl)-4-(hydroxymethyl)-2,3-O-isopropylidene-β-D-ribofuranoside

Base Information

Chemical Name:methyl 5-O-(tert-butyldiphenylsilyl)-4-(hydroxymethyl)-2,3-O-isopropylidene-β-D-ribofuranoside
CAS No.:212970-65-5
Molecular Formula:C₂₆H₃₆O₆Si
Molecular Weight:472.654
Hs Code.:

Synonyms:methyl 5-O-(tert-butyldiphenylsilyl)-4-(hydroxymethyl)-2,3-O-isopropylidene-β-D-ribofuranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl 5-O-(tert-butyldiphenylsilyl)-4-(hydroxymethyl)-2,3-O-isopropylidene-β-D-ribofuranoside

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Technology Process of methyl 5-O-(tert-butyldiphenylsilyl)-4-(hydroxymethyl)-2,3-O-isopropylidene-β-D-ribofuranoside

There total 1 articles about methyl 5-O-(tert-butyldiphenylsilyl)-4-(hydroxymethyl)-2,3-O-isopropylidene-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: 70.0%

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

: 58479-61-1
tert-butylchlorodiphenylsilane

: 212970-65-5
methyl 5-O-(tert-butyldiphenylsilyl)-4-(hydroxymethyl)-2,3-O-isopropylidene-β-D-ribofuranoside

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1016/S0040-4039(99)01998-X

Reference yield: 98.0%

: 98-59-9
p-toluenesulfonyl chloride

: 212970-65-5
methyl 5-O-(tert-butyldiphenylsilyl)-4-(hydroxymethyl)-2,3-O-isopropylidene-β-D-ribofuranoside

: 212970-66-6
methyl 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-4-(p-toluenesulfonyloxymethyl)-2,3-O-isopropylidene-β-D-ribofuranoside

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1016/S0040-4039(99)01998-X

Reference yield:

: 212970-65-5
methyl 5-O-(tert-butyldiphenylsilyl)-4-(hydroxymethyl)-2,3-O-isopropylidene-β-D-ribofuranoside

: 260439-87-0
5-(2-O,4-C-methylene-β-D-ribofuranosyl)-2-phenyloxazole

Guidance literature:: Multi-step reaction with 11 steps

1.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 17 h / 20 °C

2.1: 77 percent / TFA / tetrahydrofuran; H₂O / 0.33 h / 20 °C

3.1: 100 percent / ZnCl₂ / 2 h / 20 °C

4.1: 9 percent / DIBAH / CH₂Cl₂ / 6 h / 0 - 20 °C

5.1: 95 percent / NaN(TMS)2 / tetrahydrofuran / 3 h / 20 °C

6.1: 100 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

7.1: NaH / dimethylformamide / 0.17 h / 0 °C

7.2: 92 percent / dimethylformamide / 7 h / 20 °C

8.1: 100 percent / 10 percent HCl / H₂O; tetrahydrofuran / 2 h / 20 °C

9.1: MgBr₂ / tetrahydrofuran / 18 h / 20 °C

10.1: 90 percent / TPP; DEAD / toluene; tetrahydrofuran / 6 h / 0 - 20 °C

11.1: 46 percent / H₂ / 20 percent Pd/C / ethanol / 9 h / 20 °C

With hydrogenchloride; dmap; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; thiamine diphosphate; sodium hydride; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid; magnesium bromide; zinc(II) chloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 9.1: Grignard reaction / 10.1: Mitsunobu cyclization;
DOI:10.1016/S0040-4020(02)00226-0