3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propyl-1-azide

Base Information

Chemical Name:3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propyl-1-azide
CAS No.:1352789-28-6
Molecular Formula:C₂₇H₃₇N₃O₄Si
Molecular Weight:495.694
Hs Code.:

Synonyms:3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propyl-1-azide

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Chemical Property of 3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propyl-1-azide

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Technology Process of 3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propyl-1-azide

There total 7 articles about 3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propyl-1-azide 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: 89.0%

: 1352789-23-1
3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)prop-1-yl methanesulfonate

: 1352789-28-6
3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propyl-1-azide

Guidance literature:: With sodium azide; 18-crown-6 ether; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1055/s-0030-1260200

Reference yield:

: (1S,5R,6R,8S)-8-allyl-3,3-dimethyl-6-hydroxymethyl-2,4,7-trioxabicyclo[3.3.0]octane

: 1352789-28-6
3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propyl-1-azide

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine / 12 h / 0 - 20 °C

2.1: borane-THF / tetrahydrofuran / 3 h / 0 °C

2.2: 1.5 h / 0 - 20 °C

3.1: triethylamine / dichloromethane / 0.33 h / 5 - 20 °C

4.1: sodium azide; 18-crown-6 ether / N,N-dimethyl-formamide / 24 h / 20 °C

With pyridine; sodium azide; borane-THF; 18-crown-6 ether; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-0030-1260200

Reference yield:

: 82921-68-4
3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)prop-1-ene

: 1352789-28-6
3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propyl-1-azide

Guidance literature:: Multi-step reaction with 3 steps

1.1: borane-THF / tetrahydrofuran / 3 h / 0 °C

1.2: 1.5 h / 0 - 20 °C

2.1: triethylamine / dichloromethane / 0.33 h / 5 - 20 °C

3.1: sodium azide; 18-crown-6 ether / N,N-dimethyl-formamide / 24 h / 20 °C

With sodium azide; borane-THF; 18-crown-6 ether; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-0030-1260200