{(E)-(1S,4S)-6-[(2S,6S,8R,9S)-8-(3-benzyloxy-propyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,2,4-trimethyl-hex-2-enyloxy}-tert-butyl-dimethyl-silane

Base Information

Chemical Name:{(E)-(1S,4S)-6-[(2S,6S,8R,9S)-8-(3-benzyloxy-propyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,2,4-trimethyl-hex-2-enyloxy}-tert-butyl-dimethyl-silane
CAS No.:927396-48-3
Molecular Formula:C₃₅H₆₀O₄Si
Molecular Weight:572.945
Hs Code.:

Synonyms:{(E)-(1S,4S)-6-[(2S,6S,8R,9S)-8-(3-benzyloxy-propyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,2,4-trimethyl-hex-2-enyloxy}-tert-butyl-dimethyl-silane

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Chemical Property of {(E)-(1S,4S)-6-[(2S,6S,8R,9S)-8-(3-benzyloxy-propyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,2,4-trimethyl-hex-2-enyloxy}-tert-butyl-dimethyl-silane

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Technology Process of {(E)-(1S,4S)-6-[(2S,6S,8R,9S)-8-(3-benzyloxy-propyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,2,4-trimethyl-hex-2-enyloxy}-tert-butyl-dimethyl-silane

There total 18 articles about {(E)-(1S,4S)-6-[(2S,6S,8R,9S)-8-(3-benzyloxy-propyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,2,4-trimethyl-hex-2-enyloxy}-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: 91.0%

: C₂₉H₄₆O₄

: 69739-34-0
t-butyldimethylsiyl triflate

: 927396-48-3
{(E)-(1S,4S)-6-[(2S,6S,8R,9S)-8-(3-benzyloxy-propyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,2,4-trimethyl-hex-2-enyloxy}-tert-butyl-dimethyl-silane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.25h;
DOI:10.1021/ol702095n

Reference yield: 76.0%

: 927396-60-9
[(E)-(1S,4S,7S)-10-[(2S,5S,6R)-6-(3-benzyloxypropyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-7-(4-methoxy-benzyloxy)-1,2,4-trimethyl-dec-2-enyloxy](tert-butyl)(dimethyl)silane

: 927396-48-3
{(E)-(1S,4S)-6-[(2S,6S,8R,9S)-8-(3-benzyloxy-propyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,2,4-trimethyl-hex-2-enyloxy}-tert-butyl-dimethyl-silane

Guidance literature:: With pyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 ℃; for 25h;
DOI:10.1021/ol062957y

Reference yield:

: 5470-84-8
4-benzyloxybutanal

: 927396-48-3
{(E)-(1S,4S)-6-[(2S,6S,8R,9S)-8-(3-benzyloxy-propyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-1,2,4-trimethyl-hex-2-enyloxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 7 steps

1: 97 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / -50 °C

2: 96 percent / tetra-n-butylammonium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C

3: 81 percent / 10-camphorsulfonic acid / 120 h / 60 °C

4: 94 percent / diisobutylaluminum hydride / hexane; diethyl ether / 4.5 h / -78 °C

5: 86 percent / n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

6: 75 percent / tris(triphenylphosphine) rhodium(I) chloride; hydrogen / benzene / 18 h / 20 °C / 4137.18 Torr

7: 76 percent / pyridine; DDQ / CH₂Cl₂ / 25 h / 0 °C

With pyridine; Wilkinson's catalyst; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; tetra(n-butyl)ammonium hydroxide; hydrogen; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; benzene; 5: Wittig olefination;
DOI:10.1021/ol062957y