(Z)-(2S,5R,10S,11S)-12-Benzenesulfonyl-5-benzyloxy-10-(1-ethoxy-ethoxy)-2-hydroxy-8,11-dimethyl-1-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-dodec-7-en-6-one

Base Information

• Chemical Name: (Z)-(2S,5R,10S,11S)-12-Benzenesulfonyl-5-benzyloxy-10-(1-ethoxy-ethoxy)-2-hydroxy-8,11-dimethyl-1-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-dodec-7-en-6-one
• CAS No.: 102795-11-9
• Molecular Formula: C₃₇H₅₄O₉S
• Molecular Weight: 674.896

Synonyms:

Chemical Property of (Z)-(2S,5R,10S,11S)-12-Benzenesulfonyl-5-benzyloxy-10-(1-ethoxy-ethoxy)-2-hydroxy-8,11-dimethyl-1-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-dodec-7-en-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(2S,5R,10S,11S)-12-Benzenesulfonyl-5-benzyloxy-10-(1-ethoxy-ethoxy)-2-hydroxy-8,11-dimethyl-1-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-dodec-7-en-6-one

There total 52 articles about (Z)-(2S,5R,10S,11S)-12-Benzenesulfonyl-5-benzyloxy-10-(1-ethoxy-ethoxy)-2-hydroxy-8,11-dimethyl-1-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-dodec-7-en-6-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:

isopropyl 2,4,6-tri-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranoside (93662-86-3) → (Z)-(2S,5R,10S,11S)-12-Benzenesulfonyl-5-benzyloxy-10-(1-ethoxy-ethoxy)-2-hydroxy-8,11-dimethyl-1-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-dodec-7-en-6-one (102795-11-9)

Guidance literature:

Multi-step reaction with 14 steps

1: LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

2: 96 percent / hydrogen / 10percent Pd/C / ethyl acetate / 24 h

3: imidazole / dimethylformamide / Ambient temperature

4: 1.) sodium hydride / 1.) THF, 2.) THF, DMF, 6.5 h

5: n-Bu₄NF / tetrahydrofuran; acetonitrile

6: 1.) dimethylsulfoxide, oxalyl chloride 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) CH₂Cl₂, -78 to 0 deg C

7: CH₂Cl₂ / -20 - 20 °C

8: 79 percent / (+/-)-10-camphorsulfonic acid / 50 °C

9: diisobutylaluminum hydride / toluene / 1 h / -78 °C

10: 91 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h / Ambient temperature

11: 72 percent / benzenesulfinate, potassium iodide / dimethylformamide / 10 h / 100 °C

12: 54 percent / bromine, sodium acetate / acetic acid / 0.5 h / 0 °C

13: 1.) n-butyllithium / 1.) THF, -78 deg C, 15 min; 2.) THF, -78 deg C, 15 min.

14: 1.) CuI / 1.) ether, 0 deg C, 20 min; 2.) ether, -78 deg C, 15 min.

With 1H-imidazole; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; bromine; phenylsulphinate anion; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; potassium iodide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(01)86915-5

Reference yield:

2-propyl 3,4-dideoxy-α-D-erythro-hex-3-enopyranoside (115352-42-6) → (Z)-(2S,5R,10S,11S)-12-Benzenesulfonyl-5-benzyloxy-10-(1-ethoxy-ethoxy)-2-hydroxy-8,11-dimethyl-1-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-dodec-7-en-6-one (102795-11-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 96 percent / hydrogen / 10percent Pd/C / ethyl acetate / 24 h

2: imidazole / dimethylformamide / Ambient temperature

3: 1.) sodium hydride / 1.) THF, 2.) THF, DMF, 6.5 h

4: n-Bu₄NF / tetrahydrofuran; acetonitrile

5: 1.) dimethylsulfoxide, oxalyl chloride 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) CH₂Cl₂, -78 to 0 deg C

6: CH₂Cl₂ / -20 - 20 °C

7: 79 percent / (+/-)-10-camphorsulfonic acid / 50 °C

8: diisobutylaluminum hydride / toluene / 1 h / -78 °C

9: 91 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h / Ambient temperature

10: 72 percent / benzenesulfinate, potassium iodide / dimethylformamide / 10 h / 100 °C

11: 54 percent / bromine, sodium acetate / acetic acid / 0.5 h / 0 °C

12: 1.) n-butyllithium / 1.) THF, -78 deg C, 15 min; 2.) THF, -78 deg C, 15 min.

13: 1.) CuI / 1.) ether, 0 deg C, 20 min; 2.) ether, -78 deg C, 15 min.

With 1H-imidazole; copper(l) iodide; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; bromine; phenylsulphinate anion; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; potassium iodide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(01)86915-5

Reference yield:

2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose (3366-47-0) → (Z)-(2S,5R,10S,11S)-12-Benzenesulfonyl-5-benzyloxy-10-(1-ethoxy-ethoxy)-2-hydroxy-8,11-dimethyl-1-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-dodec-7-en-6-one (102795-11-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 63.1 percent / BF₃*Et₂O / benzene / 0.17 h / Ambient temperature

2: LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

3: 96 percent / hydrogen / 10percent Pd/C / ethyl acetate / 24 h

4: imidazole / dimethylformamide / Ambient temperature

5: 1.) sodium hydride / 1.) THF, 2.) THF, DMF, 6.5 h

6: n-Bu₄NF / tetrahydrofuran; acetonitrile

7: 1.) dimethylsulfoxide, oxalyl chloride 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min; 2.) CH₂Cl₂, -78 to 0 deg C

8: CH₂Cl₂ / -20 - 20 °C

9: 79 percent / (+/-)-10-camphorsulfonic acid / 50 °C

10: diisobutylaluminum hydride / toluene / 1 h / -78 °C

11: 91 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h / Ambient temperature

12: 72 percent / benzenesulfinate, potassium iodide / dimethylformamide / 10 h / 100 °C

13: 54 percent / bromine, sodium acetate / acetic acid / 0.5 h / 0 °C

14: 1.) n-butyllithium / 1.) THF, -78 deg C, 15 min; 2.) THF, -78 deg C, 15 min.

15: 1.) CuI / 1.) ether, 0 deg C, 20 min; 2.) ether, -78 deg C, 15 min.

With 1H-imidazole; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; bromine; phenylsulphinate anion; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; potassium iodide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)86915-5

upstream raw materials:

(R)-2-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-oxirane

(2R,3S)-4-Benzenesulfonyl-3-methyl-butane-1,2-diol

(2S,3S)-1-Benzenesulfonyl-2-methyl-hex-5-yn-3-ol

(3R,4S)-5-Benzenesulfonyl-4-methyl-pentane-1,3-diol

Downstream raw materials:

(2S,6R,8S,11R)-2-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-11-benzyloxy-4-methyl-8-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-ylmethyl)-1,7-dioxa-spiro[5.5]undec-4-ene

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