(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethyl-silyl)oxy]-1-propyl}-2-[(R)-3-ethyl-3-formylpropyl]-1,7-dioxaspiro[5.5]undecane

Base Information

• Chemical Name: (2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethyl-silyl)oxy]-1-propyl}-2-[(R)-3-ethyl-3-formylpropyl]-1,7-dioxaspiro[5.5]undecane
• CAS No.: 203063-82-5
• Molecular Formula: C₃₃H₅₄O₆Si
• Molecular Weight: 574.874
• Mol file: 203063-82-5.mol

Synonyms:(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethyl-silyl)oxy]-1-propyl}-2-[(R)-3-ethyl-3-formylpropyl]-1,7-dioxaspiro[5.5]undecane

Chemical Property of (2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethyl-silyl)oxy]-1-propyl}-2-[(R)-3-ethyl-3-formylpropyl]-1,7-dioxaspiro[5.5]undecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethyl-silyl)oxy]-1-propyl}-2-[(R)-3-ethyl-3-formylpropyl]-1,7-dioxaspiro[5.5]undecane

There total 17 articles about (2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethyl-silyl)oxy]-1-propyl}-2-[(R)-3-ethyl-3-formylpropyl]-1,7-dioxaspiro[5.5]undecane 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: 96.0%

(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)oxy]-1-propyl}-2-[(R)-3-hydroxymethyl-1-pentyl]-1,7-dioxaspiro[5.5]undecane (131704-24-0) → (2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethyl-silyl)oxy]-1-propyl}-2-[(R)-3-ethyl-3-formylpropyl]-1,7-dioxaspiro[5.5]undecane (203063-82-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 2.33333h;

DOI:10.1021/jo0104429

Reference yield:

(2S,3S,4S,6R,8S,9S)-3,9-dimethyl-8-[(R)-2-hydroxy-1-propyl]-2-[(R)-3-(hydroxymethyl)-1-pentyl]-1,7-dioxaspiro[5.5]undecan-4-ol (131725-13-8) → (2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethyl-silyl)oxy]-1-propyl}-2-[(R)-3-ethyl-3-formylpropyl]-1,7-dioxaspiro[5.5]undecane (203063-82-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 13 mg / 2,6-lutidine / CH₂Cl₂ / 2.5 h / -78 °C

2: 90 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h

3: 44 percent / hydrofluoric acid*pyridine / tetrahydrofuran; pyridine / 11 h / 20 °C

4: 96 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 2.33 h / -78 - 20 °C

With 2,6-dimethylpyridine; dmap; oxalyl dichloride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; 4: Swern oxidation;

DOI:10.1021/jo0104429

Reference yield:

(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)oxy]-1-propyl}-2-{(R)-3-[(tert-butyldimethylsilyl)oxy]methyl-1-pentyl}-1,7-dioxaspiro[5.5]undecane (189760-89-2) → (2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethyl-silyl)oxy]-1-propyl}-2-[(R)-3-ethyl-3-formylpropyl]-1,7-dioxaspiro[5.5]undecane (203063-82-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 44 percent / hydrofluoric acid*pyridine / tetrahydrofuran; pyridine / 11 h / 20 °C

2: 96 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 2.33 h / -78 - 20 °C

With oxalyl dichloride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; 2: Swern oxidation;

DOI:10.1021/jo0104429

upstream raw materials:

(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)oxy]-1-propyl}-2-[(R)-3-hydroxymethyl-1-pentyl]-1,7-dioxaspiro[5.5]undecane

3-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-octanoic acid

(2S,3S,4S,6R,8S,9S)-3,9-dimethyl-8-[(R)-2-hydroxy-1-propyl]-2-[(R)-3-(hydroxymethyl)-1-pentyl]-1,7-dioxaspiro[5.5]undecan-4-ol

tert-butyldimethylsilyl chloride

Downstream raw materials:

(2S,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)-oxy]-1-propyl}-2-[(R)-3-ethyl-5-(E)-iodo-4-pentenyl]-1,7-dioxaspiro[5.5]undecane

C₈₀H₁₅₁IO₁₂Si₅

C₇₁H₁₁₉IO₁₄SSi₂

C₇₄H₁₃₇IO₁₂Si₄