(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Base Information

• Chemical Name: (4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS No.: 925458-11-3
• Molecular Formula: C₂₉H₄₂O₄Si
• Molecular Weight: 482.736
• Mol file: 925458-11-3.mol

Synonyms:(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Chemical Property of (4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

There total 9 articles about (4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 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:

{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol (866423-21-4) → (4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (925458-11-3)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - -65 ℃;

DOI:10.1016/j.tetlet.2005.07.153

Reference yield:

(R)-8-Benzyloxy-octan-2-ol (866423-15-6) → (4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (925458-11-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / imidazole; DMAP / dimethylformamide / 2 h / 0 °C

2: 91 percent / H₂ / Pd/C / ethyl acetate / 20 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -65 °C

4: tetrahydrofuran / 6 h / Heating

5: 94 percent / K₂CO₃; K₃Fe(CN)6; MeSO₂NH₂ / (DHQ)2PHAL; OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

6: 89 percent / p-TSA / CH₂Cl₂ / 2 h

7: 85 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 - 20 °C

8: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -65 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; oxalyl dichloride; methanesulfonamide; hydrogen; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); palladium on activated charcoal; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 3: Swern oxidation / 4: Wittig reaction / 5: Sharpless asymmetric dihydroxylation / 8: Swern oxidation;

DOI:10.1016/j.tetlet.2005.07.153

Reference yield:

(R)-7-(tert-butyldiphenylsilyloxy)octanal → (4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (925458-11-3)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran / 6 h / Heating

2: 94 percent / K₂CO₃; K₃Fe(CN)6; MeSO₂NH₂ / (DHQ)2PHAL; OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

3: 89 percent / p-TSA / CH₂Cl₂ / 2 h

4: 85 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 - 20 °C

5: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -65 °C

With lithium aluminium tetrahydride; oxalyl dichloride; methanesulfonamide; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 1: Wittig reaction / 2: Sharpless asymmetric dihydroxylation / 5: Swern oxidation;

DOI:10.1016/j.tetlet.2005.07.153

upstream raw materials:

{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

(R)-8-Benzyloxy-octan-2-ol

(R)-7-((tert-butyldiphenylsilyl)oxy)octan-1-ol

(E)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-dec-2-enoic acid ethyl ester

Downstream raw materials:

cladospolide B

(Z)-3-{(4S,5S)-5-[(R)-6-(tert-butyldiphenylsilyloxy)heptyl]-2,2-dimethyl[1,3]dioxolan-4-yl}acrylic acid

(Z)-3-{(4S,5S)-5-[(R)-6-(tert-Butyl-diphenyl-silanyloxy)-heptyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester