(R)-3-((3S,4S,6R)-3-hydroxy-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptanoyl)-4-benzyloxazolin-2-one

Base Information

Chemical Name:(R)-3-((3S,4S,6R)-3-hydroxy-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptanoyl)-4-benzyloxazolin-2-one
CAS No.:918961-60-1
Molecular Formula:C₂₉H₄₉NO₅Si
Molecular Weight:519.797
Hs Code.:

Synonyms:(R)-3-((3S,4S,6R)-3-hydroxy-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptanoyl)-4-benzyloxazolin-2-one

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Chemical Property of (R)-3-((3S,4S,6R)-3-hydroxy-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptanoyl)-4-benzyloxazolin-2-one

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Technology Process of (R)-3-((3S,4S,6R)-3-hydroxy-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptanoyl)-4-benzyloxazolin-2-one

There total 1 articles about (R)-3-((3S,4S,6R)-3-hydroxy-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptanoyl)-4-benzyloxazolin-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: 78.0%

: (2S,4R)-2,4-Dimethyl-5-triisopropylsilanyloxy-pentanal

: 101711-78-8,131685-53-5
(3R)-3-propionyl-4-benzyloxazolidin-2-one

: 918961-60-1
(R)-3-((3S,4S,6R)-3-hydroxy-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptanoyl)-4-benzyloxazolin-2-one

Guidance literature:: (3R)-3-propionyl-4-benzyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h;

(2S,4R)-2,4-Dimethyl-5-triisopropylsilanyloxy-pentanal; In dichloromethane; at -78 - -10 ℃; for 2.5h;
DOI:10.1021/jo062047u

Reference yield:

: 918961-60-1
(R)-3-((3S,4S,6R)-3-hydroxy-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptanoyl)-4-benzyloxazolin-2-one

: 918961-71-4
(E)-(3R,5R,6S,7S,9R,13R,14R)-14-ethyl-6-(4-methoxybenzyloxy)-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione

Guidance literature:: Multi-step reaction with 11 steps

1.1: 88 percent / LiBH₄ / tetrahydrofuran; methanol / 0.75 h / 0 °C

2.1: 92 percent / CSA / CH₂Cl₂ / 12 h / 20 °C

3.1: 94 percent / DIBAL-H / toluene / 1 h / 0 °C

4.1: 86 percent / (COCl)2; DMSO; i-Pr₂NEt / CH₂Cl₂ / -78 - 0 °C

5.1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 1 h / 0 °C

5.2: 76 percent / CH₂Cl₂ / 4 h / -78 - -20 °C

6.1: 82 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 0 - 20 °C

7.1: Et₃N; 2,4,6-trichlorobenzoylchloride / tetrahydrofuran / 3 h / 20 °C

7.2: 61 percent / DMAP / benzene / 24 h / 20 °C

8.1: 79 percent / HF / pyridine; tetrahydrofuran / 48 h / 20 °C

9.1: 77 percent / Dess-Martin periodinane / CH₂Cl₂; pyridine / 12 h / 20 °C

10.1: CrCl₂; NiCl₂ / dimethylsulfoxide / 12 h / 20 °C

11.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 18 h / 20 °C

With pyridine; chromium dichloride; lithium hydroxide; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; hydrogen fluoride; dihydrogen peroxide; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; 4.1: Swern Oxidation / 5.2: Evans Aldol Reaction / 9.1: Dess-Martin Oxidation / 10.1: Nozaki-Hiyama-Kishi Reaction / 11.1: Dess-Martin Oxidation;
DOI:10.1021/jo062047u

Reference yield:

: 918961-60-1
(R)-3-((3S,4S,6R)-3-hydroxy-2,4,6-trimethyl-7-(triisopropylsilyloxy)heptanoyl)-4-benzyloxazolin-2-one

: 918961-72-5
(2R,3S,4S,5S,6S,8R)-((3R,4R,E)-6-iodo-4-methylhex-5-en-3-yl) 3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6,8-tetramethyl-9-oxononanoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 88 percent / LiBH₄ / tetrahydrofuran; methanol / 0.75 h / 0 °C

2.1: 92 percent / CSA / CH₂Cl₂ / 12 h / 20 °C

3.1: 94 percent / DIBAL-H / toluene / 1 h / 0 °C

4.1: 86 percent / (COCl)2; DMSO; i-Pr₂NEt / CH₂Cl₂ / -78 - 0 °C

5.1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 1 h / 0 °C

5.2: 76 percent / CH₂Cl₂ / 4 h / -78 - -20 °C

6.1: 82 percent / LiOH; H₂O₂ / tetrahydrofuran; H₂O / 0 - 20 °C

7.1: Et₃N; 2,4,6-trichlorobenzoylchloride / tetrahydrofuran / 3 h / 20 °C

7.2: 61 percent / DMAP / benzene / 24 h / 20 °C

8.1: 79 percent / HF / pyridine; tetrahydrofuran / 48 h / 20 °C

9.1: 93 percent / TEMPO; aq. NaOCl; aq. NaHCO₃ / KBr / CH₂Cl₂ / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; hydrogen fluoride; dihydrogen peroxide; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; potassium bromide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; toluene; 4.1: Swern Oxidation / 5.2: Evans Aldol Reaction;
DOI:10.1021/jo062047u