(4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester
• CAS No.: 386765-98-6
• Molecular Formula: C₄₆H₆₁NO₁₁S
• Molecular Weight: 836.056
• Mol file: 386765-98-6.mol

Synonyms:(4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

Chemical Property of (4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester

There total 20 articles about (4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl 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: 80.0%

2-(5-benzenesulfonyl-pentyl)-2-hexyl-[1,3]dioxolane (386765-96-4) + methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-bromopent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate (386765-94-2) → (4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester (386765-98-6)

Guidance literature:

2-(5-benzenesulfonyl-pentyl)-2-hexyl-[1,3]dioxolane; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-bromopent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate; In tetrahydrofuran; at -78 - 0 ℃; Further stages.;

DOI:10.1039/b104864n

Reference yield:

(R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan (79241-07-9) → (4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester (386765-98-6)

Guidance literature:

Multi-step reaction with 18 steps

1.1: aq. Hg(OAc)2 / tetrahydrofuran / 20 °C

1.2: aq. KI; NaBH₄ / tetrahydrofuran / 0 °C

1.3: aq. AcOH / 20 °C

2.1: AcCl / 0 °C

3.1: Bu₂SnO / toluene / Heating

3.2: 95 percent / CsF / dimethylformamide / 70 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

5.1: DBU; LiBr / acetonitrile / -40 °C

6.1: 93 percent / DIBAL-H / toluene / -78 °C

7.1: DBU / CH₂Cl₂ / 0 °C

8.1: K₂CO₃ / xylene / 72 h / 140 °C

9.1: O₃ / CH₂Cl₂ / -78 °C

9.2: Me₂S / CH₂Cl₂

10.1: aq. NaClO₂; NaH₂PO₄; HOSO₂NH₂ / 2-methyl-propan-2-ol / 20 °C

11.1: methanol / 20 °C

12.1: aq. HCl / tetrahydrofuran / 20 °C

13.1: toluene / 20 °C

14.1: 75 percent / DIBAL-H / toluene; tetrahydrofuran / -15 °C

15.1: 86 percent / DBU / CH₂Cl₂ / 20 °C

16.1: Et₃N / CH₂Cl₂ / 0 °C

17.1: LiBr / acetone / 20 °C

18.1: BuLi / tetrahydrofuran / -78 °C

18.2: 80 percent / tetrahydrofuran / -78 - 0 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; oxalyl dichloride; amidosulfuric acid fluoride; mercury(II) diacetate; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; acetyl chloride; lithium bromide; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; acetonitrile; xylene; tert-butyl alcohol; 4.1: Swern oxidation / 5.1: Horner-Emmons reaction / 8.1: Overmann rearrangement;

DOI:10.1039/b104864n

Reference yield:

methyl 3-O-benzyl-2-deoxy-α-D-arabino-hexofuranoside (386765-73-7) → (4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid methyl ester (386765-98-6)

Guidance literature:

Multi-step reaction with 16 steps

1.1: Bu₂SnO / toluene / Heating

1.2: 95 percent / CsF / dimethylformamide / 70 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

3.1: DBU; LiBr / acetonitrile / -40 °C

4.1: 93 percent / DIBAL-H / toluene / -78 °C

5.1: DBU / CH₂Cl₂ / 0 °C

6.1: K₂CO₃ / xylene / 72 h / 140 °C

7.1: O₃ / CH₂Cl₂ / -78 °C

7.2: Me₂S / CH₂Cl₂

8.1: aq. NaClO₂; NaH₂PO₄; HOSO₂NH₂ / 2-methyl-propan-2-ol / 20 °C

9.1: methanol / 20 °C

10.1: aq. HCl / tetrahydrofuran / 20 °C

11.1: toluene / 20 °C

12.1: 75 percent / DIBAL-H / toluene; tetrahydrofuran / -15 °C

13.1: 86 percent / DBU / CH₂Cl₂ / 20 °C

14.1: Et₃N / CH₂Cl₂ / 0 °C

15.1: LiBr / acetone / 20 °C

16.1: BuLi / tetrahydrofuran / -78 °C

16.2: 80 percent / tetrahydrofuran / -78 - 0 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; oxalyl dichloride; amidosulfuric acid fluoride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium bromide; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; acetonitrile; xylene; tert-butyl alcohol; 2.1: Swern oxidation / 3.1: Horner-Emmons reaction / 6.1: Overmann rearrangement;

DOI:10.1039/b104864n

upstream raw materials:

2-(5-benzenesulfonyl-pentyl)-2-hexyl-[1,3]dioxolane

methyl (4S,5R)-5-[(E,R)-1-benzyloxy-5-bromopent-3-en-1-yl]-4-(4-methoxybenzyloxymethyl)-2-oxooxazolidine-4-carboxylate

(R)-4-((2S,3R)-3-(benzyloxy)-2,3-dihydrofuran-2-yl)-2,2-dimethyl-1,3-dioxolan

1-bromododecan-6-one

Downstream raw materials:

(4S,5R)-5-[(E)-(R)-6-Benzenesulfonyl-1-benzyloxy-10-(2-hexyl-[1,3]dioxolan-2-yl)-dec-3-enyl]-4-(4-methoxy-benzyloxymethyl)-2-oxo-oxazolidine-4-carboxylic acid