(3R,4R,5S,6R)-4-benzoxy-6-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxypiperidin-2-one

Base Information

Chemical Name:(3R,4R,5S,6R)-4-benzoxy-6-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxypiperidin-2-one
CAS No.:666754-32-1
Molecular Formula:C₁₉H₂₉NO₆Si
Molecular Weight:395.528
Hs Code.:

Synonyms:(3R,4R,5S,6R)-4-benzoxy-6-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxypiperidin-2-one

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Chemical Property of (3R,4R,5S,6R)-4-benzoxy-6-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxypiperidin-2-one

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Technology Process of (3R,4R,5S,6R)-4-benzoxy-6-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxypiperidin-2-one

There total 7 articles about (3R,4R,5S,6R)-4-benzoxy-6-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxypiperidin-2-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: 62.0%

: 666754-31-0
(2R,3R,4S,6R)-4-benzoxy-6-(tert-butyldimethylsiloxy)-5-[[N-(phenylmethoxy)carbonyl]amino]hexanoic acid methyl ester 2,3,4,6-tetrol

: 666754-32-1
(3R,4R,5S,6R)-4-benzoxy-6-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxypiperidin-2-one

Guidance literature:: With hydrogen; palladium dihydroxide; In ethanol; acetic acid; at 20 ℃; for 10h; under 3620.04 Torr;
DOI:10.3987/com-03-s(p)12

Reference yield:

: 666754-28-5
(4R,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazoline

: 666754-32-1
(3R,4R,5S,6R)-4-benzoxy-6-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxypiperidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85 percent / NaHCO₃ / CH₂Cl₂; H₂O / 4 h / 20 °C

2.1: O₃ / ethanol / -78 °C

2.2: 87 percent / LiCl; iPr₂NEt / acetonitrile / 3 h

3.1: 80 percent / N-methylmorpholine N-oxide; OsO₄ / CH₂Cl₂; H₂O / 12 h

4.1: 62 percent / H₂ / Pd(OH)2 / ethanol; acetic acid / 10 h / 20 °C / 3620.04 Torr

With osmium(VIII) oxide; hydrogen; sodium hydrogencarbonate; ozone; 4-methylmorpholine N-oxide; palladium dihydroxide; In ethanol; dichloromethane; water; acetic acid;
DOI:10.3987/com-03-s(p)12

Reference yield:

: N-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethyl]-benzamide

: 666754-32-1
(3R,4R,5S,6R)-4-benzoxy-6-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxypiperidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

1.2: 75 percent / tetrahydrofuran / 1 h / 0 °C

2.1: 99 percent / DMAP / pyridine; CH₂Cl₂ / 12 h / 20 °C

3.1: 75 percent / K₂CO₃ / Pd(PPh₃)4 / acetonitrile / 24 h / Heating

4.1: 85 percent / NaHCO₃ / CH₂Cl₂; H₂O / 4 h / 20 °C

5.1: O₃ / ethanol / -78 °C

5.2: 87 percent / LiCl; iPr₂NEt / acetonitrile / 3 h

6.1: 80 percent / N-methylmorpholine N-oxide; OsO₄ / CH₂Cl₂; H₂O / 12 h

7.1: 62 percent / H₂ / Pd(OH)2 / ethanol; acetic acid / 10 h / 20 °C / 3620.04 Torr

With dmap; osmium(VIII) oxide; hydrogen; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; ozone; 4-methylmorpholine N-oxide; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In pyridine; ethanol; dichloromethane; water; acetic acid; acetonitrile;
DOI:10.3987/com-03-s(p)12