(2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-5-dimethyl-t-butylsiloxy-2-ethyl-3-methyl-1,7-dioxaspiro<5.5>undecan-4-ol

Base Information

• Chemical Name: (2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-5-dimethyl-t-butylsiloxy-2-ethyl-3-methyl-1,7-dioxaspiro<5.5>undecan-4-ol
• CAS No.: 105977-63-7
• Molecular Formula: C₃₃H₅₀O₆Si
• Molecular Weight: 570.842
• Mol file: 105977-63-7.mol

Synonyms:(2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-5-dimethyl-t-butylsiloxy-2-ethyl-3-methyl-1,7-dioxaspiro<5.5>undecan-4-ol

Chemical Property of (2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-5-dimethyl-t-butylsiloxy-2-ethyl-3-methyl-1,7-dioxaspiro<5.5>undecan-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-5-dimethyl-t-butylsiloxy-2-ethyl-3-methyl-1,7-dioxaspiro<5.5>undecan-4-ol

There total 14 articles about (2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-5-dimethyl-t-butylsiloxy-2-ethyl-3-methyl-1,7-dioxaspiro<5.5>undecan-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: 74.0%

(2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-4,5-dimethyldi-t-butylsiloxy-2-ethyl-3-methyl-1,7-dioxaspiro<5.5>undecane (105977-62-6) → (2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-5-dimethyl-t-butylsiloxy-2-ethyl-3-methyl-1,7-dioxaspiro<5.5>undecan-4-ol (105977-63-7)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; for 3h; Ambient temperature;

Reference yield:

pent-2-yn-1-ol (6261-22-9) → (2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-5-dimethyl-t-butylsiloxy-2-ethyl-3-methyl-1,7-dioxaspiro<5.5>undecan-4-ol (105977-63-7)

Guidance literature:

Multi-step reaction with 13 steps

1: H₂ / 5percent Pd-CaCO₃-Pb / methanol

2: 59 percent / Ti(OiPr)4, (+)-DIPT, tBuOOH / CH₂Cl₂ / -20 °C

3: 1.) EDA omplex, 2.) sodium periodate / 1.) DMSO, RT, 6 d, 2.) water

4: 93 percent / pyridine / CH₂Cl₂ / 0 °C

5: 80 percent / CSA / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 1.) lithium triethylborohydride, 2.) 30percent H₂O₂, NaOH / 1.) THF, 0 deg C, RT, 5 h, 2.) water, 0 deg C, 0.5 h

8: H₂, quinoline / Lindlar catalyst / methanol / Ambient temperature

9: 80 percent / CSA / diethyl ether

10: 56 percent / MCPBA / CH₂Cl₂ / 30 h / Ambient temperature

11: 65 percent / 5percent perchloric acid / H₂O; tetrahydrofuran / 1 h / 55 °C

12: 87 percent / 2,6-dimethylpyridine / CH₂Cl₂ / 1 h / 0 °C

13: 74 percent / camphorsulphonic acid / methanol / 3 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; sodium periodate; perchloric acid; L-(+)-diisopropyl tartrate; EDA omplex; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; lithium triethylborohydride; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; palladium on calcium fluoride poisoned with lead; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

Reference yield:

cis-2-penten-1-ol (1576-95-0) → (2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-5-dimethyl-t-butylsiloxy-2-ethyl-3-methyl-1,7-dioxaspiro<5.5>undecan-4-ol (105977-63-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 59 percent / Ti(OiPr)4, (+)-DIPT, tBuOOH / CH₂Cl₂ / -20 °C

2: 1.) EDA omplex, 2.) sodium periodate / 1.) DMSO, RT, 6 d, 2.) water

3: 93 percent / pyridine / CH₂Cl₂ / 0 °C

4: 80 percent / CSA / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 1.) lithium triethylborohydride, 2.) 30percent H₂O₂, NaOH / 1.) THF, 0 deg C, RT, 5 h, 2.) water, 0 deg C, 0.5 h

7: H₂, quinoline / Lindlar catalyst / methanol / Ambient temperature

8: 80 percent / CSA / diethyl ether

9: 56 percent / MCPBA / CH₂Cl₂ / 30 h / Ambient temperature

10: 65 percent / 5percent perchloric acid / H₂O; tetrahydrofuran / 1 h / 55 °C

11: 87 percent / 2,6-dimethylpyridine / CH₂Cl₂ / 1 h / 0 °C

12: 74 percent / camphorsulphonic acid / methanol / 3 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; sodium periodate; perchloric acid; L-(+)-diisopropyl tartrate; EDA omplex; camphor-10-sulfonic acid; hydrogen; dihydrogen peroxide; lithium triethylborohydride; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

upstream raw materials:

(2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-4,5-dimethyldi-t-butylsiloxy-2-ethyl-3-methyl-1,7-dioxaspiro<5.5>undecane

(2R,3R,4R,5R,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-2-ethyl-3-methyl-4,5-epoxy-1,7-dioxaspiro<5.5>undecane

(2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-2-ethyl-3-methyl-1,7-dioxaspiro<5.5>undecane-4,5-diol

cis-2-penten-1-ol

Downstream raw materials:

(R)-2-Methyl-hexanoic acid (2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-2-ethyl-3-methyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

(2R,3R,4R,5S,6R,8S,10S)-10-benzyloxy-8-benzyloxymethyl-2-ethyl-3-methyl-4-<(R)-methylhexanoyl>-1,7-dioxaspiro<5.5>undecan-5-ol