[3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enylsulfanyl}-1-phenyl-1H-tetrazol

Base Information

• Chemical Name: [3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enylsulfanyl}-1-phenyl-1H-tetrazol
• CAS No.: 527742-83-2
• Molecular Formula: C₂₉H₃₆N₄O₅S
• Molecular Weight: 552.695

Synonyms:[3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enylsulfanyl}-1-phenyl-1H-tetrazol

Chemical Property of [3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enylsulfanyl}-1-phenyl-1H-tetrazol

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Technology Process of [3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enylsulfanyl}-1-phenyl-1H-tetrazol

There total 17 articles about [3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enylsulfanyl}-1-phenyl-1H-tetrazol 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: 90.0%

1-Phenyl-1H-tetrazole-5-thiol (86-93-1) + [3S,4S,5E]-3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol (385809-22-3) → [3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enylsulfanyl}-1-phenyl-1H-tetrazol (527742-83-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1002/1521-3773(20011015)40:20<3842::AID-ANIE3842>3.0.CO;2-R

Reference yield:

(1S)-1-{(4R,5R)-5-[(1S)-1-hydroxy-3-methyl-3-butenyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-3-methyl-3-buten-1-ol (387392-14-5) → [3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enylsulfanyl}-1-phenyl-1H-tetrazol (527742-83-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / KOtBu / 13 / 20 °C

2: 83 percent / [P(C₆H₁₁)3]2Cl₂Ru=CHPh / CH₂Cl₂ / 5 h / 20 °C

3: 93 percent / TFA / CH₂Cl₂ / 3.5 h / 0 °C

4: Pb(OAc)4; Na₂CO₃ / CH₂Cl₂ / 0.25 h / 0 °C

5: 86 percent / LiCl; Et₃N / tetrahydrofuran / 0 - 5 °C / 2.5 Torr

6: 84.6 percent / CeCl₃*7H₂O; naBh₄ / methanol / 1 h / -95 °C

7: 100 percent / iPr₂NEt / CH₂Cl₂ / 24 h / 20 °C

8: 93 percent / TBAF / tetrahydrofuran / 0.33 h / 20 °C

9: 90 percent / DEAD; Ph₃P / tetrahydrofuran / 0.5 h / 0 - 5 °C

With lead(IV) acetate; sodium tetrahydroborate; cerium(III) chloride; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; lithium chloride; diethylazodicarboxylate; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo026743f

Reference yield:

(4S,5S)-4,5-bis-1-[(S)-allyloxy-3-methylbut-3-enyl]-2,2-dimethyl-[1,3]-dioxolane (385809-17-6) → [3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enylsulfanyl}-1-phenyl-1H-tetrazol (527742-83-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 83 percent / [P(C₆H₁₁)3]2Cl₂Ru=CHPh / CH₂Cl₂ / 5 h / 20 °C

2: 93 percent / TFA / CH₂Cl₂ / 3.5 h / 0 °C

3: Pb(OAc)4; Na₂CO₃ / CH₂Cl₂ / 0.25 h / 0 °C

4: 86 percent / LiCl; Et₃N / tetrahydrofuran / 0 - 5 °C / 2.5 Torr

5: 84.6 percent / CeCl₃*7H₂O; naBh₄ / methanol / 1 h / -95 °C

6: 100 percent / iPr₂NEt / CH₂Cl₂ / 24 h / 20 °C

7: 93 percent / TBAF / tetrahydrofuran / 0.33 h / 20 °C

8: 90 percent / DEAD; Ph₃P / tetrahydrofuran / 0.5 h / 0 - 5 °C

With lead(IV) acetate; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; lithium chloride; diethylazodicarboxylate; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo026743f

upstream raw materials:

1-Phenyl-1H-tetrazole-5-thiol

[3S,4S,5E]-3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol

(S)-4-methyl-1-trityloxymethyl-3,6-dihydro-2H-pyran

(-)-(3S)-3-[(4-methoxybenzyl)oxy]dihydrofuran-2(3H)-one

Downstream raw materials:

laulimalide

[(2S),(2S,6S,7E,10S,11S,12E),(2R,6R)]-tert-butyl-(2-{6-[10-(4-methoxybenzyloxy)-6,11-bismethoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylenetrideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}ethoxy)-dimethylsilane

[(2S),3S,4S,5E]-5-{3-(4-methoxybenzyloxy)-4-methoxymethoxy-6-[4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-enyl-1-sulfonyl}-1-phenyl-1H-tetrazol

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