Benzoic acid (R)-2-[(2S,5S,6S)-5-methyl-6-((R)-1-methyl-2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl ester

Base Information

Chemical Name:Benzoic acid (R)-2-[(2S,5S,6S)-5-methyl-6-((R)-1-methyl-2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl ester
CAS No.:851121-19-2
Molecular Formula:C₁₉H₂₆O₄
Molecular Weight:318.413
Hs Code.:

Synonyms:Benzoic acid (R)-2-[(2S,5S,6S)-5-methyl-6-((R)-1-methyl-2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl ester

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Chemical Property of Benzoic acid (R)-2-[(2S,5S,6S)-5-methyl-6-((R)-1-methyl-2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl ester

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Technology Process of Benzoic acid (R)-2-[(2S,5S,6S)-5-methyl-6-((R)-1-methyl-2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl ester

There total 14 articles about Benzoic acid (R)-2-[(2S,5S,6S)-5-methyl-6-((R)-1-methyl-2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl ester 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%

: 851121-67-0
Benzoic acid (R)-2-[(2S,5S,6S)-6-((S)-2-hydroxy-1-methyl-ethyl)-5-methyl-tetrahydro-pyran-2-yl]-propyl ester

: 851121-19-2
Benzoic acid (R)-2-[(2S,5S,6S)-5-methyl-6-((R)-1-methyl-2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl ester

Guidance literature:: With N,N-diethyl-N-isopropylamine; Chloro-oxo-acetic acid; dimethyl sulfoxide; In dichloromethane; at -78 - 50 ℃; for 0.333333h;
DOI:10.1055/s-2005-863705

Reference yield:

: 851121-23-8
(2R,3R,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-pentanal

: 851121-19-2
Benzoic acid (R)-2-[(2S,5S,6S)-5-methyl-6-((R)-1-methyl-2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: NaH / tetrahydrofuran / 1 h / -15 °C

1.2: 92 percent / tetrahydrofuran / 3 h / 0 - 22 °C

2.1: 99 percent / H₂ / Raney-nickel / ethanol / 5 h / 22 °C / 750.06 Torr

3.1: 99 percent / DIBALH / toluene; tetrahydrofuran / 2 h / -70 - 0 °C

4.1: 95 percent / oxalyl chloride; DMSO; N(i-Pr)Et₂ / CH₂Cl₂ / 0.33 h / -78 - 50 °C

5.1: 97 percent / dibutylborontriflate; Et₃N / CH₂Cl₂ / 1.5 h / -65 °C

6.1: tributyborane; propionic acid / tetrahydrofuran / 1.5 h / 22 °C

7.1: LiBH₄ / tetrahydrofuran / 14 h / 0 - 22 °C

8.1: 88 percent / pyridine / 3 h / -15 - 22 °C

9.1: 88 percent / Me₂AlCl / hexane; CH₂Cl₂ / 2 h / -25 °C

10.1: 56 percent / TPP; DEAD / toluene / 16 h / 22 °C

11.1: 95 percent / PPTS / methanol / 16 h / 22 °C

12.1: 95 percent / oxalylchloride; DMSO; N(i-Pr)Et₂ / CH₂Cl₂ / 0.33 h / -78 - 50 °C

With pyridine; lithium borohydride; oxalyl dichloride; N,N-diethyl-N-isopropylamine; tributyl borane; Chloro-oxo-acetic acid; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dimethylaluminum chloride; pyridinium p-toluenesulfonate; thiamine diphosphate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; propionic acid; triethylamine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene; 10.1: Mitsunobu cyclization;
DOI:10.1055/s-2005-863705

Reference yield:

: 851121-28-3
tert-Butyl-[(2S,3S,4S)-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyloxy]-dimethyl-silane

: 851121-19-2
Benzoic acid (R)-2-[(2S,5S,6S)-5-methyl-6-((R)-1-methyl-2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: O₃ / methanol / -78 °C

1.2: TPP / 16 h / 22 °C

2.1: NaH / tetrahydrofuran / 1 h / -15 °C

2.2: 92 percent / tetrahydrofuran / 3 h / 0 - 22 °C

3.1: 99 percent / H₂ / Raney-nickel / ethanol / 5 h / 22 °C / 750.06 Torr

4.1: 99 percent / DIBALH / toluene; tetrahydrofuran / 2 h / -70 - 0 °C

5.1: 95 percent / oxalyl chloride; DMSO; N(i-Pr)Et₂ / CH₂Cl₂ / 0.33 h / -78 - 50 °C

6.1: 97 percent / dibutylborontriflate; Et₃N / CH₂Cl₂ / 1.5 h / -65 °C

7.1: tributyborane; propionic acid / tetrahydrofuran / 1.5 h / 22 °C

8.1: LiBH₄ / tetrahydrofuran / 14 h / 0 - 22 °C

9.1: 88 percent / pyridine / 3 h / -15 - 22 °C

10.1: 88 percent / Me₂AlCl / hexane; CH₂Cl₂ / 2 h / -25 °C

11.1: 56 percent / TPP; DEAD / toluene / 16 h / 22 °C

12.1: 95 percent / PPTS / methanol / 16 h / 22 °C

13.1: 95 percent / oxalylchloride; DMSO; N(i-Pr)Et₂ / CH₂Cl₂ / 0.33 h / -78 - 50 °C

With pyridine; lithium borohydride; oxalyl dichloride; N,N-diethyl-N-isopropylamine; tributyl borane; Chloro-oxo-acetic acid; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dimethylaluminum chloride; pyridinium p-toluenesulfonate; thiamine diphosphate; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; propionic acid; triethylamine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene; 11.1: Mitsunobu cyclization;
DOI:10.1055/s-2005-863705