(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

Base Information

Chemical Name:(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
CAS No.:117169-27-4
Molecular Formula:C₃₈H₆₄O₈Si
Molecular Weight:677.007
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 13 articles about (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 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%

: 117169-28-5
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

: 117155-78-9
[(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

: 117169-27-4
(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

Guidance literature:: With methyllithium; In tetrahydrofuran; at -4 ℃; for 38h;
DOI:10.1016/S0040-4039(00)86686-1

Reference yield:

: 74243-88-2
(βS,4S)-β,2,3-trimethyl-1,3-dioxolane-4-ethanol

: 117169-27-4
(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

Guidance literature:: Multi-step reaction with 8 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

With hydrogenchloride; aluminum amalgam; n-butyllithium; ethanol; dichloromethane; water; dipyridine chromium trioxide; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)86686-1

Reference yield:

: 74213-64-2
(2S,3S)-erythro-3-methylbutane-1,2,4-triol

: 117169-27-4
(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

Guidance literature:: Multi-step reaction with 9 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

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

With hydrogenchloride; aluminum amalgam; n-butyllithium; ethanol; dichloromethane; water; hydrogen cation; dipyridine chromium trioxide; sodium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)86686-1