(4S,5S)-6-Benzyloxy-1-[(2S,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-2-(toluene-4-sulfonyl)-hexan-3-ol

Base Information

• Chemical Name: (4S,5S)-6-Benzyloxy-1-[(2S,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-2-(toluene-4-sulfonyl)-hexan-3-ol
• CAS No.: 117155-77-8
• Molecular Formula: C₄₅H₇₂O₁₀SSi
• Molecular Weight: 833.212

Synonyms:

Chemical Property of (4S,5S)-6-Benzyloxy-1-[(2S,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-2-(toluene-4-sulfonyl)-hexan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-6-Benzyloxy-1-[(2S,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-2-(toluene-4-sulfonyl)-hexan-3-ol

There total 10 articles about (4S,5S)-6-Benzyloxy-1-[(2S,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-2-(toluene-4-sulfonyl)-hexan-3-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:

(2S,3S)-4-Benzyloxy-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyraldehyde (117155-76-7) + tert-Butyl-{(2S,4S,6S,8R,9S)-8-((S)-sec-butyl)-9-methyl-2-[2-(toluene-4-sulfonyl)-ethyl]-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy}-dimethyl-silane (117169-26-3) → (4S,5S)-6-Benzyloxy-1-[(2S,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-2-(toluene-4-sulfonyl)-hexan-3-ol (117155-77-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃;

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

Reference yield:

(βS,4S)-β,2,3-trimethyl-1,3-dioxolane-4-ethanol (74243-88-2) → (4S,5S)-6-Benzyloxy-1-[(2S,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-2-(toluene-4-sulfonyl)-hexan-3-ol (117155-77-8)

Guidance literature:

Multi-step reaction with 7 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

With hydrogenchloride; n-butyllithium; ethanol; dichloromethane; water; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran;

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

Reference yield:

(2S,3S)-erythro-3-methylbutane-1,2,4-triol (74213-64-2) → (4S,5S)-6-Benzyloxy-1-[(2S,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-2-(toluene-4-sulfonyl)-hexan-3-ol (117155-77-8)

Guidance literature:

Multi-step reaction with 8 steps

1: H+

2: NaH

3: HCl, EtOH

4: Et₃N, CH₂Cl₂

5: i-Pr₂NEt

6: AcOH, H₂O / 40 °C

7: PCC

8: n-BuLi / tetrahydrofuran / -78 °C

With hydrogenchloride; n-butyllithium; ethanol; dichloromethane; water; hydrogen cation; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran;

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

upstream raw materials:

(2S,3S)-4-Benzyloxy-2-(2-methoxy-ethoxymethoxy)-3-methyl-butyraldehyde

tert-Butyl-{(2S,4S,6S,8R,9S)-8-((S)-sec-butyl)-9-methyl-2-[2-(toluene-4-sulfonyl)-ethyl]-1,7-dioxa-spiro[5.5]undec-10-en-4-yloxy}-dimethyl-silane

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

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

Downstream raw materials:

(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

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

[(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

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