[(2R,4S,6S,8R,9S)-2-[(4S,5S)-6-Benzyloxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-hex-2-ynyl]-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(2R,4S,6S,8R,9S)-2-[(4S,5S)-6-Benzyloxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-hex-2-ynyl]-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy]-tert-butyl-dimethyl-silane
• CAS No.: 117155-78-9
• Molecular Formula: C₃₈H₆₂O₇Si
• Molecular Weight: 658.992

Synonyms:

Chemical Property of [(2R,4S,6S,8R,9S)-2-[(4S,5S)-6-Benzyloxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-hex-2-ynyl]-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,4S,6S,8R,9S)-2-[(4S,5S)-6-Benzyloxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-hex-2-ynyl]-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy]-tert-butyl-dimethyl-silane

There total 15 articles about [(2R,4S,6S,8R,9S)-2-[(4S,5S)-6-Benzyloxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-hex-2-ynyl]-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy]-tert-butyl-dimethyl-silane 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: 6.0%

Trifluoro-methanesulfonic acid (2S,3S)-4-benzyloxy-1-[2-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-eth-(Z)-ylidene]-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl ester (117169-28-5) → [(2R,4S,6S,8R,9S)-2-[(4S,5S)-6-Benzyloxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-hex-2-ynyl]-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy]-tert-butyl-dimethyl-silane (117155-78-9) + (4S,5S)-6-Benzyloxy-1-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-4-(2-methoxy-ethoxymethoxy)-5-methyl-hexan-3-one (117169-27-4)

Guidance literature:

With methyllithium; In tetrahydrofuran; at -4 ℃; for 38h;

DOI:10.1016/S0040-4039(00)86686-1

Reference yield:

Trifluoro-methanesulfonic acid (2S,3S)-4-benzyloxy-1-[2-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-eth-(Z)-ylidene]-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl ester (117169-28-5) + methyl iodide (74-88-4) → [(2R,4S,6S,8R,9S)-2-[(4S,5S)-6-Benzyloxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-hex-2-ynyl]-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy]-tert-butyl-dimethyl-silane (117155-78-9) + [(2R,4S,6S,8R,9S)-2-[(E)-(4S,5S)-6-Benzyloxy-4-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-hex-2-enyl]-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy]-tert-butyl-dimethyl-silane (117155-79-0)

Guidance literature:

With CuCN; In tetrahydrofuran; at -4 ℃; for 38h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)86686-1

Reference yield:

(βS,4S)-β,2,3-trimethyl-1,3-dioxolane-4-ethanol (74243-88-2) → [(2R,4S,6S,8R,9S)-2-[(4S,5S)-6-Benzyloxy-4-(2-methoxy-ethoxymethoxy)-5-methyl-hex-2-ynyl]-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy]-tert-butyl-dimethyl-silane (117155-78-9)

Guidance literature:

Multi-step reaction with 10 steps

1: NaH

2: HCl, EtOH

3: Et₃N, CH₂Cl₂

4: i-Pr₂NEt

5: AcOH, H₂O / 40 °C

6: PCC

7: n-BuLi / tetrahydrofuran / -78 °C

8: 1.) CrO_3.2py, 2.)Al(Hg) / 1.) aq. THF, 2.)aq. THF, 65 deg C

9: 70 percent / LiN(TMS)2 / tetrahydrofuran / -78 °C

10: 63 percent / MeLi, CuCN / tetrahydrofuran / 38 h / -4 °C

With hydrogenchloride; aluminum amalgam; n-butyllithium; ethanol; dichloromethane; water; methyllithium; dipyridine chromium trioxide; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)86686-1

upstream raw materials:

Trifluoro-methanesulfonic acid (2S,3S)-4-benzyloxy-1-[2-[(2R,4S,6S,8R,9S)-8-((S)-sec-butyl)-4-(tert-butyl-dimethyl-silanyloxy)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-eth-(Z)-ylidene]-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyl ester

methyl iodide

(2S,3S)-erythro-3-methylbutane-1,2,4-triol

(βS,4S)-β,2,3-trimethyl-1,3-dioxolane-4-ethanol

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