(3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3,4-(isopropylidenedioxy)-6-(triphenylmethoxy)hex-1-yne

Base Information

Chemical Name:(3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3,4-(isopropylidenedioxy)-6-(triphenylmethoxy)hex-1-yne
CAS No.:1354520-04-9
Molecular Formula:C₃₄H₄₂O₄Si
Molecular Weight:542.791
Hs Code.:

Synonyms:(3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3,4-(isopropylidenedioxy)-6-(triphenylmethoxy)hex-1-yne

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Chemical Property of (3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3,4-(isopropylidenedioxy)-6-(triphenylmethoxy)hex-1-yne

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Technology Process of (3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3,4-(isopropylidenedioxy)-6-(triphenylmethoxy)hex-1-yne

There total 2 articles about (3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3,4-(isopropylidenedioxy)-6-(triphenylmethoxy)hex-1-yne 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: 95.0%

: 1354520-03-8
3,4-isopropylidene-6-O-triphenylmethyl-1,2-dideoxy-D-ribohex-1-ynitol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1354520-04-9
(3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3,4-(isopropylidenedioxy)-6-(triphenylmethoxy)hex-1-yne

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 72h; Inert atmosphere;
DOI:10.1021/ol203162s

Reference yield:

: 54503-64-9,54503-65-0
2,3-O-isopropylidene-5-O-trityl-D-ribofuranose

: 1354520-04-9
(3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3,4-(isopropylidenedioxy)-6-(triphenylmethoxy)hex-1-yne

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium carbonate / methanol / 8 h / 55 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 72 h / 20 °C / Inert atmosphere

With 1H-imidazole; potassium carbonate; In methanol; dichloromethane;
DOI:10.1021/ol203162s

Reference yield:

: 1354520-04-9
(3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3,4-(isopropylidenedioxy)-6-(triphenylmethoxy)hex-1-yne

: 1354520-13-0
(1R,2S,3R,4S)-4-(diallylamino)cyclohex-5-ene-1,2,3-triol

Guidance literature:: Multi-step reaction with 8 steps

1.1: iron(III) chloride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C / Inert atmosphere

3.1: sulfuric acid / 1 h / 0 °C / Inert atmosphere

4.1: N-Bromosuccinimide; silver nitrate / acetone / 2 h / 20 °C / Inert atmosphere

5.1: pyridine; potassium diazodicarboxylate; acetic acid / methanol / 14 h / Inert atmosphere

6.1: bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine / toluene / 50 °C / Inert atmosphere

7.1: sodium periodate; ammonium acetate / water; acetone / 96 h / 20 °C / Inert atmosphere

8.1: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

8.2: 192 h / 80 °C / Inert atmosphere

With pyridine; hydrogenchloride; iron(III) chloride; bis-triphenylphosphine-palladium(II) chloride; sodium periodate; N-Bromosuccinimide; sulfuric acid; ammonium acetate; potassium phenolate; water; potassium diazodicarboxylate; Dess-Martin periodane; silver nitrate; acetic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 8.2: Petasis reaction;
DOI:10.1021/ol203162s