1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)-5-phenylpent-4-yn-3-one

Base Information

Chemical Name:1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)-5-phenylpent-4-yn-3-one
CAS No.:1352789-44-6
Molecular Formula:C₂₅H₃₆O₅Si
Molecular Weight:444.643
Hs Code.:

Synonyms:1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)-5-phenylpent-4-yn-3-one

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Chemical Property of 1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)-5-phenylpent-4-yn-3-one

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Technology Process of 1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)-5-phenylpent-4-yn-3-one

There total 7 articles about 1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)-5-phenylpent-4-yn-3-one 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: 90.0%

: 1352789-40-2
(3R,S)-1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)-5-phenylpent-4-yn-3-ol

: 1352789-44-6
1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)-5-phenylpent-4-yn-3-one

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 4h; Molecular sieve; Inert atmosphere;
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

: 1352789-44-6
1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)-5-phenylpent-4-yn-3-one

Guidance literature:: Multi-step reaction with 5 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: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1.25 h / -72 - 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 4 h / 20 °C

5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 4 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

With pyridine; borane-THF; oxalyl dichloride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation / 5.1: Dess-Martin oxidation;
DOI:10.1055/s-0030-1260200

Reference yield:

: 1352789-14-0
3-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propan-1-ol

: 1352789-44-6
1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)-5-phenylpent-4-yn-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1.25 h / -72 - 20 °C / Inert atmosphere

2: tetrahydrofuran / 4 h / 20 °C

3: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 4 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

With oxalyl dichloride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxidation / 3: Dess-Martin oxidation;
DOI:10.1055/s-0030-1260200