(Z)-10-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-hex-3-enyl]-[1,3]dioxolan-4-yl}-dec-9-enoic acid ethyl ester

Base Information

• Chemical Name: (Z)-10-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-hex-3-enyl]-[1,3]dioxolan-4-yl}-dec-9-enoic acid ethyl ester
• CAS No.: 150311-80-1
• Molecular Formula: C₃₀H₄₆O₇S
• Molecular Weight: 550.757
• Mol file: 150311-80-1.mol

Synonyms:

Chemical Property of (Z)-10-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-hex-3-enyl]-[1,3]dioxolan-4-yl}-dec-9-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-10-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-hex-3-enyl]-[1,3]dioxolan-4-yl}-dec-9-enoic acid ethyl ester

There total 15 articles about (Z)-10-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-hex-3-enyl]-[1,3]dioxolan-4-yl}-dec-9-enoic acid ethyl 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:

1-{(4R,5S)-5-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-but-3-yn-1-ol → (Z)-10-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-hex-3-enyl]-[1,3]dioxolan-4-yl}-dec-9-enoic acid ethyl ester (150311-80-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi / 1.) THF, -30 deg C, 30 min 2.) HMPA a) -50 deg C, 1 h b) -50 to 10 deg C, overnight

2: 97 percent / H₂, quinoline / Pd-Pb-CaCO₃ (Lindlar catalyst) / ethyl acetate / 760 Torr

3: 70percent AcOH / 2 h / 40 °C

4: NaIO₄ / methanol; H₂O / 4 h / Ambient temperature

5: 1.) KN(SiMe₃)2 / 1.) THF, 0 deg C, 1 h 2.) -70 deg C to rt, overnight

6: pyridine / CH₂Cl₂ / Ambient temperature

With pyridine; quinoline; sodium periodate; n-butyllithium; hydrogen; potassium hexamethylsilazane; acetic acid; Pd-Pb-CaCO₃ (Lindlar catalyst); In methanol; dichloromethane; water; ethyl acetate;

DOI:10.1016/S0040-4020(01)81295-3

Reference yield:

1,2:4,5-di-O-isopropylidene-8-undecyne-D-glycero-D-manno-1,2,3,4,5,6-hexol → (Z)-10-{(4S,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-hex-3-enyl]-[1,3]dioxolan-4-yl}-dec-9-enoic acid ethyl ester (150311-80-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / H₂, quinoline / Pd-Pb-CaCO₃ (Lindlar catalyst) / ethyl acetate / 760 Torr

2: 70percent AcOH / 2 h / 40 °C

3: NaIO₄ / methanol; H₂O / 4 h / Ambient temperature

4: 1.) KN(SiMe₃)2 / 1.) THF, 0 deg C, 1 h 2.) -70 deg C to rt, overnight

5: pyridine / CH₂Cl₂ / Ambient temperature

With pyridine; quinoline; sodium periodate; hydrogen; potassium hexamethylsilazane; acetic acid; Pd-Pb-CaCO₃ (Lindlar catalyst); In methanol; dichloromethane; water; ethyl acetate;

DOI:10.1016/S0040-4020(01)81295-3

Reference yield:

4-O-benzyl-2,3-O-isopropylidene-D-threose (81801-09-4) → (Z)-10-{(4R,5S)-2,2-Dimethyl-5-[(Z)-(R)-1-(toluene-4-sulfonyloxy)-hex-3-enyl]-[1,3]dioxolan-4-yl}-dec-9-enoic acid ethyl ester (150311-80-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / Zn-dust / dimethylformamide; diethyl ether

2: 93 percent / imidazole

3: 1) n-BuLi, HMPA / 1) THF

4: 98 percent / H₂, quinoline / Pd-Pb-CaCO₃

5: 96 percent / Li, liq. NH₃

6: 1) DMSO, (COCl)2, 2) NEt₃

7: t-BuOK / tetrahydrofuran

8: 95 percent / n-Bu₄NF

9: pyridine

With pyridine; 1H-imidazole; quinoline; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; hydrogen; lithium; dimethyl sulfoxide; triethylamine; zinc; Pd-Pb-CaCO₃ (Lindlar catalyst); In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)74811-8

upstream raw materials:

(Z)-10-[(4R,5R)-5-((Z)-(R)-1-Hydroxy-hex-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-dec-9-enoic acid ethyl ester

p-toluenesulfonyl chloride

ethyl 11(S),12(R)-O-isopropylidene-11,12,13(R)-trihydroxy-octadeca-9,15(Z)-dienoate

4-O-benzyl-2,3-O-isopropylidene-D-threose

Downstream raw materials:

(11S,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxyoctadeca-9,15-dienoic acid methyl ester