Acetic acid (1R,2R,3S,4S)-3-acetoxy-1-[(R)-1-{(4R,5R,6R)-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-oxo-2-(2-oxo-oxazolidin-3-yl)-ethyl]-2,4-dimethyl-hex-5-enyl ester

Base Information

• Chemical Name: Acetic acid (1R,2R,3S,4S)-3-acetoxy-1-[(R)-1-{(4R,5R,6R)-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-oxo-2-(2-oxo-oxazolidin-3-yl)-ethyl]-2,4-dimethyl-hex-5-enyl ester
• CAS No.: 121425-44-3
• Molecular Formula: C₄₃H₆₁NO₁₀Si
• Molecular Weight: 780.044

Synonyms:

Chemical Property of Acetic acid (1R,2R,3S,4S)-3-acetoxy-1-[(R)-1-{(4R,5R,6R)-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-oxo-2-(2-oxo-oxazolidin-3-yl)-ethyl]-2,4-dimethyl-hex-5-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of Acetic acid (1R,2R,3S,4S)-3-acetoxy-1-[(R)-1-{(4R,5R,6R)-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-oxo-2-(2-oxo-oxazolidin-3-yl)-ethyl]-2,4-dimethyl-hex-5-enyl ester

There total 10 articles about Acetic acid (1R,2R,3S,4S)-3-acetoxy-1-[(R)-1-{(4R,5R,6R)-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-oxo-2-(2-oxo-oxazolidin-3-yl)-ethyl]-2,4-dimethyl-hex-5-enyl 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:

(2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2,4-dimethyl-3-((triethylsilyl)oxy)pentanal (106568-13-2,121440-66-2) → Acetic acid (1R,2R,3S,4S)-3-acetoxy-1-[(R)-1-{(4R,5R,6R)-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-oxo-2-(2-oxo-oxazolidin-3-yl)-ethyl]-2,4-dimethyl-hex-5-enyl ester (121425-44-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) Bu₂BOTf, Et₃N, 2.) H₂O₂ / 1.) CH₂Cl₂, from -78 deg C to -50 deg C, 2.) pH 7

2: pTsOH, H₂O / tetrahydrofuran

3: pTsOH

4: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C

5: CrCl₂ / tetrahydrofuran / -25 °C

6: pyridine

7: 1.) O₃, 2.) Me₂S / methanol / -20 °C

9: pyridine

With pyridine; chromium dichloride; dimethylsulfide; di-n-butylboryl trifluoromethanesulfonate; water; dihydrogen peroxide; toluene-4-sulfonic acid; ozone; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1021/jo00274a008

Reference yield:

3-[(2S,3R,4R,5R,6R)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-4,6-dimethyl-2-vinyl-heptanoyl]-oxazolidin-2-one → Acetic acid (1R,2R,3S,4S)-3-acetoxy-1-[(R)-1-{(4R,5R,6R)-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-oxo-2-(2-oxo-oxazolidin-3-yl)-ethyl]-2,4-dimethyl-hex-5-enyl ester (121425-44-3)

Guidance literature:

Multi-step reaction with 7 steps

1: pTsOH

2: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C

3: CrCl₂ / tetrahydrofuran / -25 °C

4: pyridine

5: 1.) O₃, 2.) Me₂S / methanol / -20 °C

7: pyridine

With pyridine; chromium dichloride; dimethylsulfide; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; methanol;

DOI:10.1021/jo00274a008

Reference yield:

3-((S)-2-{(4R,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-but-3-enoyl)-oxazolidin-2-one (121471-29-2) → Acetic acid (1R,2R,3S,4S)-3-acetoxy-1-[(R)-1-{(4R,5R,6R)-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-oxo-2-(2-oxo-oxazolidin-3-yl)-ethyl]-2,4-dimethyl-hex-5-enyl ester (121425-44-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C

2: CrCl₂ / tetrahydrofuran / -25 °C

3: pyridine

4: 1.) O₃, 2.) Me₂S / methanol / -20 °C

6: pyridine

With pyridine; chromium dichloride; dimethylsulfide; ozone; In tetrahydrofuran; methanol;

DOI:10.1021/jo00274a008

upstream raw materials:

acetic anhydride

(2R,3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2,4-dimethyl-3-((triethylsilyl)oxy)pentanal

3-((S)-2-{(4R,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-but-3-enoyl)-oxazolidin-2-one

(R)-2-{(4R,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-oxo-3-(2-oxo-oxazolidin-3-yl)-propionaldehyde

Downstream raw materials:

Acetic acid (1R,2R,3R,4R)-3-acetoxy-1-[(R)-1-{(4R,5R,6R)-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-oxo-2-(2-oxo-oxazolidin-3-yl)-ethyl]-2,4-dimethyl-5-oxo-pentyl ester

Acetic acid (1R,2R,3R,4R)-3-acetoxy-1-[(R)-1-{(4R,5R,6R)-6-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-oxo-2-(2-oxo-oxazolidin-3-yl)-ethyl]-5,5-dimethoxy-2,4-dimethyl-pentyl ester

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