(2S,3S,4R,7R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-9-(4-methoxy-benzyloxy)-3,7-dimethyl-non-5-yn-4-ol

Base Information

Chemical Name:(2S,3S,4R,7R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-9-(4-methoxy-benzyloxy)-3,7-dimethyl-non-5-yn-4-ol
CAS No.:158817-28-8
Molecular Formula:C₂₄H₃₆O₅
Molecular Weight:404.547
Hs Code.:

Synonyms:(2S,3S,4R,7R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-9-(4-methoxy-benzyloxy)-3,7-dimethyl-non-5-yn-4-ol

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Chemical Property of (2S,3S,4R,7R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-9-(4-methoxy-benzyloxy)-3,7-dimethyl-non-5-yn-4-ol

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Technology Process of (2S,3S,4R,7R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-9-(4-methoxy-benzyloxy)-3,7-dimethyl-non-5-yn-4-ol

There total 14 articles about (2S,3S,4R,7R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-9-(4-methoxy-benzyloxy)-3,7-dimethyl-non-5-yn-4-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:

: (2S,3S,7R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-9-(4-methoxy-benzyloxy)-3,7-dimethyl-non-5-yn-4-one

: (2S,3S,4S,7R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-9-(4-methoxy-benzyloxy)-3,7-dimethyl-non-5-yn-4-ol

: 158817-28-8
(2S,3S,4R,7R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-9-(4-methoxy-benzyloxy)-3,7-dimethyl-non-5-yn-4-ol

Guidance literature:: With lithium tri-t-butoxyaluminum hydride; In diethyl ether; at 0 ℃; for 3h; Yield given. Yields of byproduct given;
DOI:10.1246/cl.1994.1611

Reference yield:

: 158817-21-1
(E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol

: 158817-28-8
(2S,3S,4R,7R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-9-(4-methoxy-benzyloxy)-3,7-dimethyl-non-5-yn-4-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 94 percent / L-(+)-diethyl tartarate, Ti(OPr-i)4, t-BuOOH, molecular sieves 4A / CH₂Cl₂ / 20 h / -20 °C

2: 77 percent / hexane; CH₂Cl₂ / 16 h / 0 - 20 °C

3: NaIO₄ / tetrahydrofuran; H₂O / 0.17 h / Ambient temperature

4: PPh₃ / CH₂Cl₂ / 0.33 h / 0 °C

5: 87 percent / BuLi / tetrahydrofuran / 30 h / -78 °C

6: 1.) BuLi, THF -78 deg C, 30 min, 2.) -78 deg C, 1h

7: pyridinium dichromate

8: LiAlH(OBu-t)3 / diethyl ether / 3 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; dipyridinium dichromate; n-butyllithium; diethyl (2R,3R)-tartrate; 4 A molecular sieve; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water;
DOI:10.1246/cl.1994.1611

Reference yield:

: 146986-42-7
((2S,3S)-3-(2-(4-methoxybenzyloxy)ethyl) oxiran-2-yl)methanol

: 158817-28-8
(2S,3S,4R,7R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-9-(4-methoxy-benzyloxy)-3,7-dimethyl-non-5-yn-4-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 77 percent / hexane; CH₂Cl₂ / 16 h / 0 - 20 °C

2: NaIO₄ / tetrahydrofuran; H₂O / 0.17 h / Ambient temperature

3: PPh₃ / CH₂Cl₂ / 0.33 h / 0 °C

4: 87 percent / BuLi / tetrahydrofuran / 30 h / -78 °C

5: 1.) BuLi, THF -78 deg C, 30 min, 2.) -78 deg C, 1h

6: pyridinium dichromate

7: LiAlH(OBu-t)3 / diethyl ether / 3 h / 0 °C

With sodium periodate; dipyridinium dichromate; n-butyllithium; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water;
DOI:10.1246/cl.1994.1611