(1'S,2'R,4S,5R)-4-<2'-(Benzyloxy)-1'-<(tert-butyldimethylsilyl)oxy>-3'-oxopropyl>-3-(tert-butyldimethylsilyl)-5-methyl-2-oxazolidinone

Base Information

• Chemical Name: (1'S,2'R,4S,5R)-4-<2'-(Benzyloxy)-1'-<(tert-butyldimethylsilyl)oxy>-3'-oxopropyl>-3-(tert-butyldimethylsilyl)-5-methyl-2-oxazolidinone
• CAS No.: 147425-40-9
• Molecular Formula: C₂₆H₄₅NO₅Si₂
• Molecular Weight: 507.818

Synonyms:(1'S,2'R,4S,5R)-4-<2'-(Benzyloxy)-1'-<(tert-butyldimethylsilyl)oxy>-3'-oxopropyl>-3-(tert-butyldimethylsilyl)-5-methyl-2-oxazolidinone

Chemical Property of (1'S,2'R,4S,5R)-4-<2'-(Benzyloxy)-1'-<(tert-butyldimethylsilyl)oxy>-3'-oxopropyl>-3-(tert-butyldimethylsilyl)-5-methyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,2'R,4S,5R)-4-<2'-(Benzyloxy)-1'-<(tert-butyldimethylsilyl)oxy>-3'-oxopropyl>-3-(tert-butyldimethylsilyl)-5-methyl-2-oxazolidinone

There total 18 articles about (1'S,2'R,4S,5R)-4-<2'-(Benzyloxy)-1'-<(tert-butyldimethylsilyl)oxy>-3'-oxopropyl>-3-(tert-butyldimethylsilyl)-5-methyl-2-oxazolidinone 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%

(1'S,2'R,4S,5R)-4-<2'-(Benzyloxy)-1'-<(tert-butyldimethylsilyl)oxy>-3'-hydroxypropyl>-3-(tert-butyldimethylsilyl)-5-methyl-2-oxazolidinone (147425-39-6) → (1'S,2'R,4S,5R)-4-<2'-(Benzyloxy)-1'-<(tert-butyldimethylsilyl)oxy>-3'-oxopropyl>-3-(tert-butyldimethylsilyl)-5-methyl-2-oxazolidinone (147425-40-9)

Guidance literature:

With pyridine; chromium(VI) oxide;

DOI:10.1016/0040-4039(93)85088-E

Reference yield:

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) → (1'S,2'R,4S,5R)-4-<2'-(Benzyloxy)-1'-<(tert-butyldimethylsilyl)oxy>-3'-oxopropyl>-3-(tert-butyldimethylsilyl)-5-methyl-2-oxazolidinone (147425-40-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 90 percent / pyridine / 1.) 0 deg C to r.t., 2.) r.t., 4 h

2: 94 percent / CF₃COOH / methanol; H₂O / 20 h / Ambient temperature

3: 92 percent / pyridine / 12 h / 3 °C

4: 94 percent / NaI / butan-2-one / 2 h / Heating

5: 91 percent / Zn, glacial CH₃COOH / diethyl ether / 5 h

6: 90 percent / NaN₃ / dimethylformamide / 6 h / Heating

7: SnCl₂, Et₃N, PhSH / acetonitrile / 1 h

8: aq. NaHCO₃ / CH₂Cl₂ / 18 h

9: trifluoroacetic acid / 2 h / 80 °C

10: aq. H₂O₂, 2 M NaOH / tetrahydrofuran / 1 h

11: 1.) NaBH₄, 2.) KH / 1.) EtOH, r.t., 14 h, 2.) benzene, reflux, 20 h

12: 85 percent / 2,4,6-collidine / 12 h / Ambient temperature

13: aq. HF / acetonitrile / 2 h

14: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C to -55 deg C, 30 min, 2.) CH₂Cl₂, -55 deg C, 10 min then -55 deg C to r.t.

With pyridine; 2,4,6-trimethyl-pyridine; sodium hydroxide; sodium tetrahydroborate; sodium azide; oxalyl dichloride; hydrogen fluoride; dihydrogen peroxide; potassium hydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; thiophenol; triethylamine; trifluoroacetic acid; sodium iodide; tin(ll) chloride; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; butanone;

DOI:10.1021/jo00094a040

Reference yield:

(1'S,2'S,4R,5R)-4-<2'-(Benzyloxy)-1',3'-dihydropropyl>-5-methyl-2-oxazolidinone (147425-38-5) → (1'S,2'R,4S,5R)-4-<2'-(Benzyloxy)-1'-<(tert-butyldimethylsilyl)oxy>-3'-oxopropyl>-3-(tert-butyldimethylsilyl)-5-methyl-2-oxazolidinone (147425-40-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / 2,4,6-collidine / 12 h / Ambient temperature

2: aq. HF / acetonitrile / 2 h

3: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C to -55 deg C, 30 min, 2.) CH₂Cl₂, -55 deg C, 10 min then -55 deg C to r.t.

With 2,4,6-trimethyl-pyridine; oxalyl dichloride; hydrogen fluoride; dimethyl sulfoxide; triethylamine; In acetonitrile;

DOI:10.1021/jo00094a040

upstream raw materials:

(1'S,2'R,4S,5R)-4-<2'-(Benzyloxy)-1'-<(tert-butyldimethylsilyl)oxy>-3'-hydroxypropyl>-3-(tert-butyldimethylsilyl)-5-methyl-2-oxazolidinone

benzyl bromide

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

(1'S,2'S,4R,5R)-4-<2'-(Benzyloxy)-1',3'-dihydropropyl>-5-methyl-2-oxazolidinone

Downstream raw materials:

(4S,5R)-3-(tert-Butyl-dimethyl-silanyl)-4-[(1S,2S,3R)-1-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-5-phenylsulfanylmethyl-hex-5-enyl]-5-methyl-oxazolidin-2-one

(4S,5R)-4-[(1S,2S,3R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-5-phenylsulfanylmethyl-hex-5-enyl]-3-(tert-butyl-dimethyl-silanyl)-5-methyl-oxazolidin-2-one

(4R,5R)-4-{(S)-[(4R,5R)-2,2-Dimethyl-5-(2-phenylsulfanylmethyl-allyl)-[1,3]dioxolan-4-yl]-hydroxy-methyl}-5-methyl-oxazolidin-2-one

(1'S,2'R,3'R,4S,5R)-5-<2'-Hydroxy-1'-<(4-methylphenyl)methanesulfonamido>propyl>-3,4-(2-propylidenedioxy)cyclohexanone

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 147425-40-9 (1'S,2'R,4S,5R)-4-<2'-(Benzyloxy)-1'-<(tert-butyldimethylsilyl)oxy>-3'-oxopropyl>-3-(tert-butyldimethylsilyl)-5-methyl-2-oxazolidinone

Send

Send

Metric Ton KG G Pound L ML

Send

Send