(1'S,2'S,3'R,4S,5R)-3,1'-O-(Thiocarbonyl)-4-<1'-hydroxy-5'-<(phenylthio)methyl>-2',3'-(2-propylidenedioxy)-5'-hexenyl>-5-methyl-2-oxazolidinone

Base Information

• Chemical Name: (1'S,2'S,3'R,4S,5R)-3,1'-O-(Thiocarbonyl)-4-<1'-hydroxy-5'-<(phenylthio)methyl>-2',3'-(2-propylidenedioxy)-5'-hexenyl>-5-methyl-2-oxazolidinone
• CAS No.: 147425-43-2
• Molecular Formula: C₂₁H₂₅NO₅S₂
• Molecular Weight: 435.565

Synonyms:

Chemical Property of (1'S,2'S,3'R,4S,5R)-3,1'-O-(Thiocarbonyl)-4-<1'-hydroxy-5'-<(phenylthio)methyl>-2',3'-(2-propylidenedioxy)-5'-hexenyl>-5-methyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,2'S,3'R,4S,5R)-3,1'-O-(Thiocarbonyl)-4-<1'-hydroxy-5'-<(phenylthio)methyl>-2',3'-(2-propylidenedioxy)-5'-hexenyl>-5-methyl-2-oxazolidinone

There total 19 articles about (1'S,2'S,3'R,4S,5R)-3,1'-O-(Thiocarbonyl)-4-<1'-hydroxy-5'-<(phenylthio)methyl>-2',3'-(2-propylidenedioxy)-5'-hexenyl>-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:

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) → (1'S,2'S,3'R,4S,5R)-3,1'-O-(Thiocarbonyl)-4-<1'-hydroxy-5'-<(phenylthio)methyl>-2',3'-(2-propylidenedioxy)-5'-hexenyl>-5-methyl-2-oxazolidinone (147425-43-2)

Guidance literature:

Multi-step reaction with 17 steps

1: 90 percent / pyridine / Ambient temperature

2: 90 percent / F₃CCO₂H / methanol; H₂O / Heating

3: 95 percent / pyridine / 3 - 5 °C

4: 1) NaI, 2) Zn, AcOH / 1) EtCOMe, reflux, 2) ether, rt

5: 90 percent / NaN₃ / dimethylformamide / Heating

6: SnCl₂, Et₃N / various solvent(s)

7: NaHCO₃

8: 1) F₃CCO₂H, Ac₂O, 2) NaOH, H₂O₂ / 2) MeOH

9: NaBH₄ / ethanol

10: KH / benzene

11: collidine

12: aq. HF / acetonitrile

13: 95 percent / CrO₃, pyridine

14: 1) TiCl₄, 2) BBr₃

15: p-TsOH

16: Bu₄NF / acetonitrile

With pyridine; chromium(VI) oxide; 2,3,5-trimethyl-pyridine; sodium hydroxide; sodium tetrahydroborate; sodium azide; hydrogen fluoride; tetrabutyl ammonium fluoride; dihydrogen peroxide; acetic anhydride; boron tribromide; titanium tetrachloride; potassium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; trifluoroacetic acid; sodium iodide; tin(ll) chloride; zinc; In methanol; ethanol; water; N,N-dimethyl-formamide; acetonitrile; benzene;

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

Reference yield:

[(1S,2S,3S)-3-Benzyloxy-2,4-dihydroxy-1-((R)-1-hydroxy-ethyl)-butyl]-carbamic acid ethyl ester (158548-94-8) → (1'S,2'S,3'R,4S,5R)-3,1'-O-(Thiocarbonyl)-4-<1'-hydroxy-5'-<(phenylthio)methyl>-2',3'-(2-propylidenedioxy)-5'-hexenyl>-5-methyl-2-oxazolidinone (147425-43-2)

Guidance literature:

Multi-step reaction with 8 steps

1: KH / benzene

2: collidine

3: aq. HF / acetonitrile

4: 95 percent / CrO₃, pyridine

5: 1) TiCl₄, 2) BBr₃

6: p-TsOH

7: Bu₄NF / acetonitrile

With pyridine; chromium(VI) oxide; 2,3,5-trimethyl-pyridine; hydrogen fluoride; tetrabutyl ammonium fluoride; boron tribromide; titanium tetrachloride; potassium hydride; toluene-4-sulfonic acid; In acetonitrile; benzene;

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

Reference yield:

Benzoic acid (2R,3S,4S,5R,6S)-3-amino-5-benzyloxy-6-methoxy-2-methyl-tetrahydro-pyran-4-yl ester → (1'S,2'S,3'R,4S,5R)-3,1'-O-(Thiocarbonyl)-4-<1'-hydroxy-5'-<(phenylthio)methyl>-2',3'-(2-propylidenedioxy)-5'-hexenyl>-5-methyl-2-oxazolidinone (147425-43-2)

Guidance literature:

Multi-step reaction with 11 steps

1: NaHCO₃

2: 1) F₃CCO₂H, Ac₂O, 2) NaOH, H₂O₂ / 2) MeOH

3: NaBH₄ / ethanol

4: KH / benzene

5: collidine

6: aq. HF / acetonitrile

7: 95 percent / CrO₃, pyridine

8: 1) TiCl₄, 2) BBr₃

9: p-TsOH

10: Bu₄NF / acetonitrile

With pyridine; chromium(VI) oxide; 2,3,5-trimethyl-pyridine; sodium hydroxide; sodium tetrahydroborate; hydrogen fluoride; tetrabutyl ammonium fluoride; dihydrogen peroxide; acetic anhydride; boron tribromide; titanium tetrachloride; potassium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; trifluoroacetic acid; In ethanol; acetonitrile; benzene;

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

upstream raw materials:

(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

1,1'-Thiocarbonyldiimidazole

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:

(1'R,2'S,3'R,4S,5R)-4-<5'-Oxo-2',3'-(2-propylidenedioxy)cyclohexyl>-5-methyl-3-<(4-methylphenyl)methanesulfonyl>-2-oxazolidinone

(1'R,2'S,3'R,4S,5R)-4-<5'-Methylidene-2',3'-(2-propylidenedioxy)cyclohexyl>-5-methyl-3-<(4-methylphenyl)methanesulfonyl>-2-oxazolidinone

5,6-O-(2-Propylidene)-N-desalanyl-N-<(4-methylphenyl)methanesulfonyl>actinobolin

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

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