(2S,6S,8S)-6-Hydroxy-2,8-bis-(4-methoxy-benzyloxy)-1-((4S,6S)-6-{(4R,6R)-6-[(E)-(3S,4S)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-11-trimethylsilanyl-undec-10-yn-4-one

Base Information

• Chemical Name: (2S,6S,8S)-6-Hydroxy-2,8-bis-(4-methoxy-benzyloxy)-1-((4S,6S)-6-{(4R,6R)-6-[(E)-(3S,4S)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-11-trimethylsilanyl-undec-10-yn-4-one
• CAS No.: 676549-19-2
• Molecular Formula: C₅₉H₈₆O₁₂Si
• Molecular Weight: 1015.41

Synonyms:(2S,6S,8S)-6-Hydroxy-2,8-bis-(4-methoxy-benzyloxy)-1-((4S,6S)-6-{(4R,6R)-6-[(E)-(3S,4S)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-11-trimethylsilanyl-undec-10-yn-4-one

Chemical Property of (2S,6S,8S)-6-Hydroxy-2,8-bis-(4-methoxy-benzyloxy)-1-((4S,6S)-6-{(4R,6R)-6-[(E)-(3S,4S)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-11-trimethylsilanyl-undec-10-yn-4-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2S,6S,8S)-6-Hydroxy-2,8-bis-(4-methoxy-benzyloxy)-1-((4S,6S)-6-{(4R,6R)-6-[(E)-(3S,4S)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-11-trimethylsilanyl-undec-10-yn-4-one

There total 22 articles about (2S,6S,8S)-6-Hydroxy-2,8-bis-(4-methoxy-benzyloxy)-1-((4S,6S)-6-{(4R,6R)-6-[(E)-(3S,4S)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-11-trimethylsilanyl-undec-10-yn-4-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:

2,2-dimethoxy-propane (77-76-9) → (2S,6S,8S)-6-Hydroxy-2,8-bis-(4-methoxy-benzyloxy)-1-((4S,6S)-6-{(4R,6R)-6-[(E)-(3S,4S)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-11-trimethylsilanyl-undec-10-yn-4-one (676549-19-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 545 mg / TsOH*H₂O; 3 Angstroem molecular sieves / 21 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 2.5 h / -78 - -40 °C

2.2: Bf₃*Et₂O / tetrahydrofuran; hexane / 0.17 h / -78 °C

2.3: 59 percent / tetrahydrofuran; hexane / 3 h / -78 °C

3.1: 100 °C

4.1: Pt(DVDS) / tetrahydrofuran; xylene / 20 °C

5.1: aq. H₂O₂; KF; KHCO₃ / tetrahydrofuran; methanol / 20 °C

With potassium fluoride; n-butyllithium; bis(η2:η2-1,3-divinyltetramethyl)platinum(0); 3 A molecular sieve; dihydrogen peroxide; potassium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; xylene;

DOI:10.1021/ja039618+

Reference yield:

(2R)-1-chloro-2-hydroxy-4-pentene (197899-19-7) → (2S,6S,8S)-6-Hydroxy-2,8-bis-(4-methoxy-benzyloxy)-1-((4S,6S)-6-{(4R,6R)-6-[(E)-(3S,4S)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-11-trimethylsilanyl-undec-10-yn-4-one (676549-19-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 81 percent / KOH

2.1: n-BuLi / tetrahydrofuran / -78 - 20 °C

2.2: BF₃*Et₂O / tetrahydrofuran / 0.33 h / -78 °C

2.3: 75 percent / tetrahydrofuran / 1 h / -78 °C

3.1: 77 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

4.1: NaH / dimethylformamide / 0.17 h

4.2: 73 percent / Bu₄NI / dimethylformamide / 25 h / 20 °C

5.1: n-BuLi / tetrahydrofuran / 0.17 h / -50 °C

5.2: 434 mg / tetrahydrofuran / 0.5 h / -40 °C

6.1: 32 percent / (S,S)-salen Co(III)OAc; H₂O / tetrahydrofuran / 1 h

7.1: n-BuLi / tetrahydrofuran; hexane / 2.5 h / -78 - -40 °C

7.2: Bf₃*Et₂O / tetrahydrofuran; hexane / 0.17 h / -78 °C

7.3: 59 percent / tetrahydrofuran; hexane / 3 h / -78 °C

8.1: 100 °C

9.1: Pt(DVDS) / tetrahydrofuran; xylene / 20 °C

10.1: aq. H₂O₂; KF; KHCO₃ / tetrahydrofuran; methanol / 20 °C

With potassium fluoride; potassium hydroxide; n-butyllithium; bis(η2:η2-1,3-divinyltetramethyl)platinum(0); (S,S)-salen Co(III)OAc; water; dihydrogen peroxide; sodium hydride; potassium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; xylene;

DOI:10.1021/ja039618+

Reference yield:

(R)-2-but-3-enyloxirane (144422-60-6) → (2S,6S,8S)-6-Hydroxy-2,8-bis-(4-methoxy-benzyloxy)-1-((4S,6S)-6-{(4R,6R)-6-[(E)-(3S,4S)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-11-trimethylsilanyl-undec-10-yn-4-one (676549-19-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-BuLi / tetrahydrofuran / -78 - 20 °C

1.2: BF₃*Et₂O / tetrahydrofuran / 0.33 h / -78 °C

1.3: 75 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 77 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

3.1: NaH / dimethylformamide / 0.17 h

3.2: 73 percent / Bu₄NI / dimethylformamide / 25 h / 20 °C

4.1: n-BuLi / tetrahydrofuran / 0.17 h / -50 °C

4.2: 434 mg / tetrahydrofuran / 0.5 h / -40 °C

5.1: 32 percent / (S,S)-salen Co(III)OAc; H₂O / tetrahydrofuran / 1 h

6.1: n-BuLi / tetrahydrofuran; hexane / 2.5 h / -78 - -40 °C

6.2: Bf₃*Et₂O / tetrahydrofuran; hexane / 0.17 h / -78 °C

6.3: 59 percent / tetrahydrofuran; hexane / 3 h / -78 °C

7.1: 100 °C

8.1: Pt(DVDS) / tetrahydrofuran; xylene / 20 °C

9.1: aq. H₂O₂; KF; KHCO₃ / tetrahydrofuran; methanol / 20 °C

With potassium fluoride; n-butyllithium; bis(η2:η2-1,3-divinyltetramethyl)platinum(0); (S,S)-salen Co(III)OAc; water; dihydrogen peroxide; sodium hydride; potassium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; xylene;

DOI:10.1021/ja039618+

upstream raw materials:

2,2-dimethoxy-propane

(2R)-1-chloro-2-hydroxy-4-pentene

(R)-2-but-3-enyloxirane

(4S,5S)-4,6-dimethyl-5-(p-methoxybenzyloxy)-trans-hept-2-enal

Downstream raw materials:

C₅₉H₈₄O₁₂

C₅₉H₈₅IO₁₂

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