(S)-3-[(S)-2-[(2R,4R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,6-dimethyl-tetrahydro-pyran-2-yl]-2-(3,4-dimethoxy-benzyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one

Base Information

• Chemical Name: (S)-3-[(S)-2-[(2R,4R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,6-dimethyl-tetrahydro-pyran-2-yl]-2-(3,4-dimethoxy-benzyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one
• CAS No.: 1054698-71-3
• Molecular Formula: C₃₀H₄₉NO₉Si
• Molecular Weight: 595.806
• Mol file: 1054698-71-3.mol

Synonyms:(S)-3-[(S)-2-[(2R,4R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,6-dimethyl-tetrahydro-pyran-2-yl]-2-(3,4-dimethoxy-benzyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one

Chemical Property of (S)-3-[(S)-2-[(2R,4R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,6-dimethyl-tetrahydro-pyran-2-yl]-2-(3,4-dimethoxy-benzyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(S)-2-[(2R,4R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,6-dimethyl-tetrahydro-pyran-2-yl]-2-(3,4-dimethoxy-benzyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one

There total 15 articles about (S)-3-[(S)-2-[(2R,4R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,6-dimethyl-tetrahydro-pyran-2-yl]-2-(3,4-dimethoxy-benzyloxy)-acetyl]-4-isopropyl-oxazolidin-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:

(2S,5R,6S,7R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-1-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-6-methyl-octane-1,3-dione (185300-92-9) → (S)-3-[(S)-2-[(2R,4R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,6-dimethyl-tetrahydro-pyran-2-yl]-2-(3,4-dimethoxy-benzyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one (1054698-71-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 24h; Ambient temperature;

DOI:10.1021/jo961841k

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (S)-3-[(S)-2-[(2R,4R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,6-dimethyl-tetrahydro-pyran-2-yl]-2-(3,4-dimethoxy-benzyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one (1054698-71-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) 0 deg C, 30 min

2: 1.) 4-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, toluene, 1.5 h, 2.) t-BuOH, THF, H₂O, toluene, 30 min

3: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min, 2.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 -> 0 deg C

5: H₂ / Pd/C / methanol / 24 h / Ambient temperature

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jo961841k

Reference yield:

(R)-3-((2S,3R)-3-Hydroxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one (104486-82-0) → (S)-3-[(S)-2-[(2R,4R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-5,6-dimethyl-tetrahydro-pyran-2-yl]-2-(3,4-dimethoxy-benzyloxy)-acetyl]-4-isopropyl-oxazolidin-2-one (1054698-71-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 87 percent / triflic acid / cyclohexane; CH₂Cl₂ / 1 h

2: 1.) H₂O, LiBH₄, 2.) aq. NaOH / 1.) Et₂O, THF, 0 deg C - 1 h, 23 deg C - 1 h, 2.) Et₂O, THF, 23 deg C, 1 h

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C -> 0 deg C

4: 74 percent / TiCl₄ / CH₂Cl₂ / 16 h / -78 °C

5: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) 0 deg C, 30 min

6: 1.) 4-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, toluene, 1.5 h, 2.) t-BuOH, THF, H₂O, toluene, 30 min

7: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min, 2.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min

8: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 -> 0 deg C

9: H₂ / Pd/C / methanol / 24 h / Ambient temperature

With 2,6-dimethylpyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium borohydride; oxalyl dichloride; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; water; hydrogen; titanium tetrachloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; cyclohexane;

DOI:10.1021/jo961841k

upstream raw materials:

(2S,5R,6S,7R)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-1-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-6-methyl-octane-1,3-dione

t-butyldimethylsiyl triflate

(R)-3-((2S,3R)-3-Hydroxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one

(3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate

Downstream raw materials:

(S)-(3,4-Dimethoxy-benzyloxy)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetic acid methyl ester

7-(3,4-dimethoxybenzyl)pederic acid