5-{(1S,2S,3R)-2-[(1E,4E)-(R)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hexa-1,4-dienyl]-3-methyl-cyclopropylmethanesulfonyl}-1-phenyl-1H-tetrazole

Base Information

• Chemical Name: 5-{(1S,2S,3R)-2-[(1E,4E)-(R)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hexa-1,4-dienyl]-3-methyl-cyclopropylmethanesulfonyl}-1-phenyl-1H-tetrazole
• CAS No.: 380355-86-2
• Molecular Formula: C₂₇H₃₆N₄O₃S
• Molecular Weight: 496.674

Synonyms:5-{(1S,2S,3R)-2-[(1E,4E)-(R)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hexa-1,4-dienyl]-3-methyl-cyclopropylmethanesulfonyl}-1-phenyl-1H-tetrazole

Chemical Property of 5-{(1S,2S,3R)-2-[(1E,4E)-(R)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hexa-1,4-dienyl]-3-methyl-cyclopropylmethanesulfonyl}-1-phenyl-1H-tetrazole

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Technology Process of 5-{(1S,2S,3R)-2-[(1E,4E)-(R)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hexa-1,4-dienyl]-3-methyl-cyclopropylmethanesulfonyl}-1-phenyl-1H-tetrazole

There total 14 articles about 5-{(1S,2S,3R)-2-[(1E,4E)-(R)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hexa-1,4-dienyl]-3-methyl-cyclopropylmethanesulfonyl}-1-phenyl-1H-tetrazole 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:

5-{(1S,2S,3R)-2-[(1E,4E)-(R)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hexa-1,4-dienyl]-3-methyl-cyclopropylmethylsulfanyl}-1-phenyl-1H-tetrazole → 5-{(1S,2S,3R)-2-[(1E,4E)-(R)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hexa-1,4-dienyl]-3-methyl-cyclopropylmethanesulfonyl}-1-phenyl-1H-tetrazole (380355-86-2)

Guidance literature:

With ammonium molybdate; dihydrogen peroxide; In tetrahydrofuran; ethanol; at 20 ℃;

DOI:10.1021/ja016893s

Reference yield:

trans-3-methyl-3-hexen-2-one (1567-77-7) → 5-{(1S,2S,3R)-2-[(1E,4E)-(R)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hexa-1,4-dienyl]-3-methyl-cyclopropylmethanesulfonyl}-1-phenyl-1H-tetrazole (380355-86-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: Et₃N / diethyl ether / 2 h

2.1: 87 percent / (1R,2S)-ligand-chromium / 40 h / 20 °C

3.1: BH₃*THF / tetrahydrofuran / 0 - 20 °C

3.2: 70 percent / aq. HCl / tetrahydrofuran / 3 h / Heating

4.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

4.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: 71 percent / tetrahydrofuran; hexane / -78 - 20 °C

6.1: Bu₃SnCu(Bu)CNLi₂ / tetrahydrofuran; hexane / 0.25 h / -78 °C

6.2: DMPU / tetrahydrofuran; hexane / -78 - 20 °C

6.3: 80 percent / I₂ / diethyl ether / 0 - 20 °C

7.1: 88 percent / Pd(PPh₃)4 / benzene; tetrahydrofuran / 0.5 h / 60 - 70 °C

8.1: H₂; Rh(acac)(CO)2; (S,R)-BINAPHOS / benzene / 60 h / 30 - 35 °C / 15201 Torr

9.1: 190 mg / CrCl₂ / tetrahydrofuran / 20 °C

10.1: 96 percent / Pd(OAc)2; Ag₂CO₃; Et₃N / CH₂Cl₂ / 24 h / 20 °C

11.1: 99 percent / DIBAL-H / toluene / 0.5 h / -78 °C

12.1: 86 percent / (R,R)-1,2-dimethylamido-ethylenedioxy-butyl-borane / CH₂Cl₂ / 2 h / -10 °C

13.1: PPh₃; DEAD / tetrahydrofuran / 3 h / 20 °C

14.1: 93 mg / ammonium molybdate; aq. H₂O₂ / ethanol; tetrahydrofuran / 20 °C

With chromium dichloride; palladium diacetate; acetylacetonatodicarbonylrhodium(l); tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium molybdate; borane-THF; oxalyl dichloride; nBu₃Sn(nBu)Cu(CN)Li₂; (S,R)-o-BINAPHOS; (1R,2S)-ligand-chromium; (R,R)-1,2-dimethylamido-ethylenedioxy-butyl-borane; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; benzene; 2.1: hetero-Diels-Alder reaction / 7.1: Kumada coupling / 8.1: Nozaki hydroformylation / 9.1: Takai olefination / 10.1: Heck raection / 12.1: Simmons-Smith reaction / 13.1: Mitsunobu reaction;

DOI:10.1021/ja016893s

Reference yield:

(2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde (380355-91-9) → 5-{(1S,2S,3R)-2-[(1E,4E)-(R)-5-((2R,6R)-6-Ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hexa-1,4-dienyl]-3-methyl-cyclopropylmethanesulfonyl}-1-phenyl-1H-tetrazole (380355-86-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 71 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: Bu₃SnCu(Bu)CNLi₂ / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.2: DMPU / tetrahydrofuran; hexane / -78 - 20 °C

2.3: 80 percent / I₂ / diethyl ether / 0 - 20 °C

3.1: 88 percent / Pd(PPh₃)4 / benzene; tetrahydrofuran / 0.5 h / 60 - 70 °C

4.1: H₂; Rh(acac)(CO)2; (S,R)-BINAPHOS / benzene / 60 h / 30 - 35 °C / 15201 Torr

5.1: 190 mg / CrCl₂ / tetrahydrofuran / 20 °C

6.1: 96 percent / Pd(OAc)2; Ag₂CO₃; Et₃N / CH₂Cl₂ / 24 h / 20 °C

7.1: 99 percent / DIBAL-H / toluene / 0.5 h / -78 °C

8.1: 86 percent / (R,R)-1,2-dimethylamido-ethylenedioxy-butyl-borane / CH₂Cl₂ / 2 h / -10 °C

9.1: PPh₃; DEAD / tetrahydrofuran / 3 h / 20 °C

10.1: 93 mg / ammonium molybdate; aq. H₂O₂ / ethanol; tetrahydrofuran / 20 °C

With chromium dichloride; palladium diacetate; acetylacetonatodicarbonylrhodium(l); tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonium molybdate; nBu₃Sn(nBu)Cu(CN)Li₂; (S,R)-o-BINAPHOS; (R,R)-1,2-dimethylamido-ethylenedioxy-butyl-borane; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; benzene; 3.1: Kumada coupling / 4.1: Nozaki hydroformylation / 5.1: Takai olefination / 6.1: Heck raection / 8.1: Simmons-Smith reaction / 9.1: Mitsunobu reaction;

DOI:10.1021/ja016893s

upstream raw materials:

trans-3-methyl-3-hexen-2-one

(2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde

((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)methanol

(2R,6R)-6-Ethyl-2-ethynyl-5-methyl-3,6-dihydro-2H-pyran

Downstream raw materials:

(+)-ambruticin S

2-{5-[2-(2-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-yl}-vinyl)-3-methyl-cyclopropyl]-1,3-dimethyl-penta-1,4-dienyl}-6-ethyl-5-methyl-3,6-dihydro-2H-pyran

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