(4S,5R,6S,8R)-9-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-methoxy-4,8-dimethylnon-2-yn-5-ol

Base Information

• Chemical Name: (4S,5R,6S,8R)-9-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-methoxy-4,8-dimethylnon-2-yn-5-ol
• CAS No.: 1601460-60-9
• Molecular Formula: C₂₆H₃₃BrO₄
• Molecular Weight: 489.45

Synonyms:(4S,5R,6S,8R)-9-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-methoxy-4,8-dimethylnon-2-yn-5-ol

Chemical Property of (4S,5R,6S,8R)-9-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-methoxy-4,8-dimethylnon-2-yn-5-ol

Chemical Property:

Purity/Quality:

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Technology Process of (4S,5R,6S,8R)-9-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-methoxy-4,8-dimethylnon-2-yn-5-ol

There total 10 articles about (4S,5R,6S,8R)-9-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-methoxy-4,8-dimethylnon-2-yn-5-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,4R)-5-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-2-methoxy-4-methylpentanal (869732-16-1) + M-(-)-2-(tributylstannyl)-2,3-pentadiene → (4S,5R,6S,8R)-9-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-methoxy-4,8-dimethylnon-2-yn-5-ol (1601460-60-9) + (6S,8R)-9-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-methoxy-4,8-dimethylnon-2-yn-5-ol

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 0.5h; Overall yield = 78 %; Overall yield = 1.08 g; Inert atmosphere;

DOI:10.1016/j.tet.2014.03.020

Reference yield:

(2S,4R)-5-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-1-((tert-butyldimethylsilyl)oxy)-4-methylpentan-2-ol (1601460-57-4) → (4S,5R,6S,8R)-9-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-methoxy-4,8-dimethylnon-2-yn-5-ol (1601460-60-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 8.5 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

2.1: pyridine hydrogenfluoride; pyridine / acetonitrile / 2.5 h / 0 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 - 20 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

With pyridine; oxalyl dichloride; boron trifluoride diethyl etherate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; pyridine hydrogenfluoride; dimethyl sulfoxide; In dichloromethane; acetonitrile; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;

DOI:10.1016/j.tet.2014.03.020

Reference yield:

(((2S,4R)-5-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-2-methoxy-4-methylpentyl)oxy)(tert-butyl)dimethylsilane (1601460-58-5) → (4S,5R,6S,8R)-9-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-methoxy-4,8-dimethylnon-2-yn-5-ol (1601460-60-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine hydrogenfluoride; pyridine / acetonitrile / 2.5 h / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 - 20 °C / Inert atmosphere

3.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

With pyridine; oxalyl dichloride; boron trifluoride diethyl etherate; pyridine hydrogenfluoride; dimethyl sulfoxide; In dichloromethane; acetonitrile; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;

DOI:10.1016/j.tet.2014.03.020

upstream raw materials:

(2S,4R)-5-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-1-((tert-butyldimethylsilyl)oxy)-4-methylpentan-2-ol

(((2S,4R)-5-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-2-methoxy-4-methylpentyl)oxy)(tert-butyl)dimethylsilane

(2S,4R)-5-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-2-methoxy-4-methylpentan-1-ol

(2S,4R)-5-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-2-methoxy-4-methylpentanal

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