(3S,4S)-14-(tert-butyldiphenylsilyloxy)-1,3,4-tetradecanetriol

Base Information

• Chemical Name: (3S,4S)-14-(tert-butyldiphenylsilyloxy)-1,3,4-tetradecanetriol
• CAS No.: 332095-62-2
• Molecular Formula: C₃₀H₄₈O₄Si
• Molecular Weight: 500.794
• Mol file: 332095-62-2.mol

Synonyms:(3S,4S)-14-(tert-butyldiphenylsilyloxy)-1,3,4-tetradecanetriol

Chemical Property of (3S,4S)-14-(tert-butyldiphenylsilyloxy)-1,3,4-tetradecanetriol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-14-(tert-butyldiphenylsilyloxy)-1,3,4-tetradecanetriol

There total 6 articles about (3S,4S)-14-(tert-butyldiphenylsilyloxy)-1,3,4-tetradecanetriol 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: 98.0%

(4S,5S)-5-[10-(tert-butyldiphenylsilyloxy)decyl]-4,5-dihydro-4-hydroxy-2(3H)-furanone (332095-60-0) → (3S,4S)-14-(tert-butyldiphenylsilyloxy)-1,3,4-tetradecanetriol (332095-62-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1039/b002905j

Reference yield:

12-((tert-butyldiphenylsilyl)oxy)dodecan-1-ol (166170-71-4) → (3S,4S)-14-(tert-butyldiphenylsilyloxy)-1,3,4-tetradecanetriol (332095-62-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / oxalylic chloride; DMSO; NEt₃ / CH₂Cl₂ / 2 h / -40 - 0 °C

2: NEt₃ / 90 °C

3: 68 percent / K3Fe(CN)6; K2CO3; methanesulfoneamide / α-1,4-bis(dihydroquininyl)phthalazine; K2OsO4 / methanol; 2-methyl-propan-2-ol / 96 h / 0 °C

4: 98 percent / LiAlH₄ / tetrahydrofuran / -78 - 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; methanesulfonamide; potassium carbonate; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); potassium osmate(VI); α-1,4-bis(dihydroquininyl)phthalazine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; 2: Knoevenagel condensation;

DOI:10.1039/b002905j

Reference yield:

methyl E-14-(tert-butyldiphenylsilyloxy)-3-tetradecenoate (332095-61-1) → (3S,4S)-14-(tert-butyldiphenylsilyloxy)-1,3,4-tetradecanetriol (332095-62-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / K3Fe(CN)6; K2CO3; methanesulfoneamide / α-1,4-bis(dihydroquininyl)phthalazine; K2OsO4 / methanol; 2-methyl-propan-2-ol / 96 h / 0 °C

2: 98 percent / LiAlH₄ / tetrahydrofuran / -78 - 20 °C

With lithium aluminium tetrahydride; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); potassium osmate(VI); α-1,4-bis(dihydroquininyl)phthalazine; In tetrahydrofuran; methanol; tert-butyl alcohol;

DOI:10.1039/b002905j

upstream raw materials:

(4S,5S)-5-[10-(tert-butyldiphenylsilyloxy)decyl]-4,5-dihydro-4-hydroxy-2(3H)-furanone

methyl E-14-(tert-butyldiphenylsilyloxy)-3-tetradecenoate

1,12-dodecandiol

tert-butylchlorodiphenylsilane

Downstream raw materials:

(4'S,5'S)-2-{5-[10-(tert-butyldiphenylsilyloxy)decyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethanol

(4S,5S)-4-[10-(tert-butyldiphenylsilyloxy)decyl]-2,2-dimethyl-5-(2-iodoethyl)-1,3-dioxolane

(4S,5S)-Z,Z-4-[10-(tert-butyldiphenylsilyloxy)decyl]-5-(3,7-eicosadienyl)-2,2-dimethyl-1,3-dioxolane