(4S,6R,10S)-4,10-Bis-(4-methoxy-benzyloxy)-11-((4R,6R)-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)-1-trimethylsilanyl-undeca-1,8-diyn-6-ol

Base Information

Chemical Name:(4S,6R,10S)-4,10-Bis-(4-methoxy-benzyloxy)-11-((4R,6R)-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)-1-trimethylsilanyl-undeca-1,8-diyn-6-ol
CAS No.:676549-17-0
Molecular Formula:C₅₉H₈₄O₁₁Si
Molecular Weight:997.395
Hs Code.:

(4S,6R,10S)-4,10-Bis-(4-methoxy-benzyloxy)-11-((4R,6R)-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)-1-trimethylsilanyl-undeca-1,8-diyn-6-ol

Synonyms:(4S,6R,10S)-4,10-Bis-(4-methoxy-benzyloxy)-11-((4R,6R)-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)-1-trimethylsilanyl-undeca-1,8-diyn-6-ol

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Chemical Property of (4S,6R,10S)-4,10-Bis-(4-methoxy-benzyloxy)-11-((4R,6R)-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)-1-trimethylsilanyl-undeca-1,8-diyn-6-ol

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Technology Process of (4S,6R,10S)-4,10-Bis-(4-methoxy-benzyloxy)-11-((4R,6R)-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)-1-trimethylsilanyl-undeca-1,8-diyn-6-ol

There total 19 articles about (4S,6R,10S)-4,10-Bis-(4-methoxy-benzyloxy)-11-((4R,6R)-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)-1-trimethylsilanyl-undeca-1,8-diyn-6-ol 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: 59.0%

: 676548-99-5
[(S)-4-(4-Methoxy-benzyloxy)-5-(S)-oxiranyl-pent-1-ynyl]-trimethyl-silane

: 676549-15-8
C₄₁H₅₈O₈

: 676549-17-0
(4S,6R,10S)-4,10-Bis-(4-methoxy-benzyloxy)-11-((4R,6R)-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)-1-trimethylsilanyl-undeca-1,8-diyn-6-ol

Guidance literature:: C₄₁H₅₈O₈; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -40 ℃; for 2.5h;

With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;

[(S)-4-(4-Methoxy-benzyloxy)-5-(S)-oxiranyl-pent-1-ynyl]-trimethyl-silane; In tetrahydrofuran; hexane; at -78 ℃; for 3h;
DOI:10.1021/ja039618+

Reference yield:

: 77-76-9
2,2-dimethoxy-propane

: 676549-17-0
(4S,6R,10S)-4,10-Bis-(4-methoxy-benzyloxy)-11-((4R,6R)-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)-1-trimethylsilanyl-undeca-1,8-diyn-6-ol

Guidance literature:: Multi-step reaction with 2 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

With n-butyllithium; 3 A molecular sieve; toluene-4-sulfonic acid; In tetrahydrofuran; hexane;
DOI:10.1021/ja039618+

Reference yield:

: 197899-19-7
(2R)-1-chloro-2-hydroxy-4-pentene

: 676549-17-0
(4S,6R,10S)-4,10-Bis-(4-methoxy-benzyloxy)-11-((4R,6R)-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)-1-trimethylsilanyl-undeca-1,8-diyn-6-ol

Guidance literature:: Multi-step reaction with 7 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

With potassium hydroxide; n-butyllithium; (S,S)-salen Co(III)OAc; water; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja039618+