(6R^*,5R^*,3S^*,4S^*)-8-(benzyloxy)-6-<(tert-butyldimethylsilyl)oxy>-5-methoxy-3-methyl-1-octen-4-ol

Base Information

• Chemical Name: (6R^*,5R^*,3S^*,4S^*)-8-(benzyloxy)-6-<(tert-butyldimethylsilyl)oxy>-5-methoxy-3-methyl-1-octen-4-ol
• CAS No.: 116376-33-1
• Molecular Formula: C₂₃H₄₀O₄Si
• Molecular Weight: 408.654

Synonyms:(6R^*,5R^*,3S^*,4S^*)-8-(benzyloxy)-6-<(tert-butyldimethylsilyl)oxy>-5-methoxy-3-methyl-1-octen-4-ol

Chemical Property of (6R^*,5R^*,3S^*,4S^*)-8-(benzyloxy)-6-<(tert-butyldimethylsilyl)oxy>-5-methoxy-3-methyl-1-octen-4-ol

Chemical Property:

Purity/Quality:

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Technology Process of (6R^*,5R^*,3S^*,4S^*)-8-(benzyloxy)-6-<(tert-butyldimethylsilyl)oxy>-5-methoxy-3-methyl-1-octen-4-ol

There total 6 articles about (6R^*,5R^*,3S^*,4S^*)-8-(benzyloxy)-6-<(tert-butyldimethylsilyl)oxy>-5-methoxy-3-methyl-1-octen-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: 68.3%

(E)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69611-02-5) + (3R*,2S*)-5-(benzyloxy)-3-<(tert-butyldimethylsilyl)ocy>-2-methoxypentanal (116405-73-3) → (6R*,5R*,3S*,4S*)-8-(benzyloxy)-6-<(tert-butyldimethylsilyl)oxy>-5-methoxy-3-methyl-1-octen-4-ol (116376-33-1)

Guidance literature:

In dichloromethane;

DOI:10.1021/jo00256a023

Reference yield:

3-Benzyloxypropanal (19790-60-4) → (6R*,5R*,3S*,4S*)-8-(benzyloxy)-6-<(tert-butyldimethylsilyl)oxy>-5-methoxy-3-methyl-1-octen-4-ol (116376-33-1)

Guidance literature:

Multi-step reaction with 5 steps

2: 75.4 percent / imidazole, benzyl alcohol / dimethylformamide / 48 h / Ambient temperature

3: 85 percent / N-methylmorpholine N-oxide, tert-butyl alcohol, OsO₄ / acetone; H₂O / Ambient temperature

4: 100 percent / aq. NaIO₄ / acetone / 8 h / Ambient temperature

5: 68.3 percent / CH₂Cl₂

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; benzyl alcohol; tert-butyl alcohol; In dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00256a023

Reference yield:

(4R*,3R*)-1-(benzyloxy)-4-methoxy-5-hexen-3-ol (116376-13-7,116376-46-6,116497-21-3) → (6R*,5R*,3S*,4S*)-8-(benzyloxy)-6-<(tert-butyldimethylsilyl)oxy>-5-methoxy-3-methyl-1-octen-4-ol (116376-33-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 75.4 percent / imidazole, benzyl alcohol / dimethylformamide / 48 h / Ambient temperature

2: 85 percent / N-methylmorpholine N-oxide, tert-butyl alcohol, OsO₄ / acetone; H₂O / Ambient temperature

3: 100 percent / aq. NaIO₄ / acetone / 8 h / Ambient temperature

4: 68.3 percent / CH₂Cl₂

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; benzyl alcohol; tert-butyl alcohol; In dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00256a023

upstream raw materials:

(E)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(3R^*,2S^*)-5-(benzyloxy)-3-<(tert-butyldimethylsilyl)ocy>-2-methoxypentanal

3-Benzyloxypropanal

(4R^*,3R^*)-1-(benzyloxy)-4-methoxy-5-hexen-3-ol

Downstream raw materials:

(3S,4R,5R,6R)-1-Benzyloxy-4-methoxy-6-methyl-oct-7-ene-3,5-diol

(4R,5S,6S)-4-(2-Benzyloxy-ethyl)-5-methoxy-2,2-dimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxane

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