(5S,6R)-6-[(1S,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-butyl]-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-one

Base Information

• Chemical Name: (5S,6R)-6-[(1S,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-butyl]-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-one
• CAS No.: 116376-40-0
• Molecular Formula: C₃₁H₅₆O₆Si₂
• Molecular Weight: 580.953

Synonyms:(5S,6R)-6-[(1S,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-butyl]-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-one

Chemical Property of (5S,6R)-6-[(1S,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-butyl]-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R)-6-[(1S,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-butyl]-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-one

There total 8 articles about (5S,6R)-6-[(1S,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-butyl]-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-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: 66.5%

(5S,6R)-6-[(1S,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-butyl]-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-ol → (5S,6R)-6-[(1S,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-butyl]-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-one (116376-40-0)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 4h;

DOI:10.1021/jo00256a023

Reference yield:

3-Benzyloxypropanal (19790-60-4) → (5S,6R)-6-[(1S,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-butyl]-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-one (116376-40-0)

Guidance literature:

Multi-step reaction with 7 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: CH₂Cl₂ / 0 - 40 °C

6: 92 percent / H₂, Rh₂(OAc)4, triphenylphosphine / ethyl acetate / 16 h / 100 °C / 18565.6 Torr

7: 66.5 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h

With 1H-imidazole; dirhodium tetraacetate; sodium periodate; osmium(VIII) oxide; hydrogen; 4-methylmorpholine N-oxide; triphenylphosphine; pyridinium chlorochromate; benzyl alcohol; tert-butyl alcohol; In dichloromethane; water; ethyl acetate; 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) → (5S,6R)-6-[(1S,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-butyl]-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-one (116376-40-0)

Guidance literature:

Multi-step reaction with 6 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: CH₂Cl₂ / 0 - 40 °C

5: 92 percent / H₂, Rh₂(OAc)4, triphenylphosphine / ethyl acetate / 16 h / 100 °C / 18565.6 Torr

6: 66.5 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h

With 1H-imidazole; dirhodium tetraacetate; sodium periodate; osmium(VIII) oxide; hydrogen; 4-methylmorpholine N-oxide; triphenylphosphine; pyridinium chlorochromate; benzyl alcohol; tert-butyl alcohol; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00256a023

upstream raw materials:

3-Benzyloxypropanal

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

tert-butyldimethylsilyl chloride

(4R^*,3R^*)-6-(benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>-3-methoxy-1-hexene

Downstream raw materials:

(S)-4-[(4R,5R,6S)-6-(2-Benzyloxy-ethyl)-5-methoxy-2,2-dimethyl-[1,3]dioxan-4-yl]-6-(tert-butyl-diphenyl-silanyloxy)-2-methyl-hexan-1-ol

(3R,5R,6S)-6-((1S,2R)-4-Benzyloxy-2-hydroxy-1-methoxy-butyl)-5-(2-hydroxy-ethyl)-3-methyl-tetrahydro-pyran-2-one

(3R,5S,6R)-6-[(1S,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-butyl]-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-one

(3S,5S,6R)-6-[(1S,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-butyl]-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-one

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