6-O-tert-butyldimethylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-(p-tosyl)-D-ribo-hexitol

Base Information

Chemical Name:6-O-tert-butyldimethylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-(p-tosyl)-D-ribo-hexitol
CAS No.:540510-11-0
Molecular Formula:C₂₂H₃₈O₇SSi
Molecular Weight:474.691
Hs Code.:

Synonyms:6-O-tert-butyldimethylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-(p-tosyl)-D-ribo-hexitol

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Chemical Property of 6-O-tert-butyldimethylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-(p-tosyl)-D-ribo-hexitol

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Technology Process of 6-O-tert-butyldimethylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-(p-tosyl)-D-ribo-hexitol

There total 5 articles about 6-O-tert-butyldimethylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-(p-tosyl)-D-ribo-hexitol 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: 44.0%

: 98-59-9
p-toluenesulfonyl chloride

: 540510-13-2
(R)-2-((tert-butyldimethylsilyl)oxy)-1-((4R,5S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol

: 540510-11-0
6-O-tert-butyldimethylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-(p-tosyl)-D-ribo-hexitol

Guidance literature:: With pyridine; at 0 ℃; for 12h;
DOI:10.1002/chem.200390110

Reference yield:

: 217309-46-1
5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose

: 540510-11-0
6-O-tert-butyldimethylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-(p-tosyl)-D-ribo-hexitol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 74 percent / NaNH₂ / tetrahydrofuran / 6 h / 20 °C

2.1: 95 percent / pyridine / 0 - 25 °C

3.1: BH₃*THF / tetrahydrofuran / 13 h / 0 - 25 °C

3.2: 45 percent / NaOH; aq. H₂O₂ / tetrahydrofuran; ethanol / 2 h / 55 °C

4.1: 100 percent / aq. K₂CO₃ / methanol / 25 °C

5.1: 44 percent / pyridine / 12 h / 0 °C

With pyridine; borane-THF; potassium carbonate; sodium amide; In tetrahydrofuran; methanol;
DOI:10.1002/chem.200390110

Reference yield:

: 116669-77-3
(1R,4'R,5'S)-(-)-1-(2',2'-dimethyl-5'-vinyl-1',3'-dioxolan-4'-yl)-2-(tert-butyldimethylsilyloxy)-1(R)-ethan-1-ol

: 540510-11-0
6-O-tert-butyldimethylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-(p-tosyl)-D-ribo-hexitol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / pyridine / 0 - 25 °C

2.1: BH₃*THF / tetrahydrofuran / 13 h / 0 - 25 °C

2.2: 45 percent / NaOH; aq. H₂O₂ / tetrahydrofuran; ethanol / 2 h / 55 °C

3.1: 100 percent / aq. K₂CO₃ / methanol / 25 °C

4.1: 44 percent / pyridine / 12 h / 0 °C

With pyridine; borane-THF; potassium carbonate; In tetrahydrofuran; methanol;
DOI:10.1002/chem.200390110