Acetic acid (E)-(S)-1-[(2S,5S,6R)-6-((S)-2-methoxy-3-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-5-methyl-hex-2-enyl ester

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Chemical Name:Acetic acid (E)-(S)-1-[(2S,5S,6R)-6-((S)-2-methoxy-3-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-5-methyl-hex-2-enyl ester
CAS No.:618096-84-7
Molecular Formula:C₄₄H₇₆O₈Si
Molecular Weight:761.168
Hs Code.:

Acetic acid (E)-(S)-1-[(2S,5S,6R)-6-((S)-2-methoxy-3-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-5-methyl-hex-2-enyl ester

Synonyms:Acetic acid (E)-(S)-1-[(2S,5S,6R)-6-((S)-2-methoxy-3-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-5-methyl-hex-2-enyl ester

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Chemical Property of Acetic acid (E)-(S)-1-[(2S,5S,6R)-6-((S)-2-methoxy-3-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-5-methyl-hex-2-enyl ester

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Technology Process of Acetic acid (E)-(S)-1-[(2S,5S,6R)-6-((S)-2-methoxy-3-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-5-methyl-hex-2-enyl ester

There total 21 articles about Acetic acid (E)-(S)-1-[(2S,5S,6R)-6-((S)-2-methoxy-3-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-5-methyl-hex-2-enyl ester 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: 100.0%

: 108-24-7
acetic anhydride

: 618096-86-9
(E)-(S)-1-[(2S,5S,6R)-6-((S)-2-Methoxy-3-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol

: 618096-84-7
Acetic acid (E)-(S)-1-[(2S,5S,6R)-6-((S)-2-methoxy-3-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-5-methyl-hex-2-enyl ester

Guidance literature:: With pyridine; dmap; In dichloromethane; at 0 ℃; for 24h;
DOI:10.1016/S0040-4020(03)00814-7

Reference yield:

: 193416-33-0
Triethyl-[(E)-5-(4-methoxy-benzyloxy)-1-methylene-pent-2-enyloxy]-silane

: 618096-84-7
Acetic acid (E)-(S)-1-[(2S,5S,6R)-6-((S)-2-methoxy-3-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-5-methyl-hex-2-enyl ester

Guidance literature:: Multi-step reaction with 18 steps

1.1: 4 Angstroem molecular sieves / (1S,2R)-1-amino-2-indanol-derived tridentate Cr catalyst / 12 h / 20 °C

1.2: 80 percent / conc. HCl / CHCl₃ / 4 h

2.1: NaBH₄ / methanol / 1 h / 20 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

4.1: 10-camphorsulfonic acid / CH₂Cl₂; methanol / 1 h / 20 °C

5.1: pyridine / CH₂Cl₂ / 1 h / -10 °C

6.1: LDA; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C

6.2: tetrahydrofuran; hexane / -78 - 20 °C

7.1: K₂CO₃ / methanol / 12 h / 20 °C

8.1: 86 percent / pyridinium p-toluenesulfonate; Hg(OAc)2; H₂O / tetrahydrofuran / 1.5 h / 45 °C

9.1: Et₃N; c-Hex₂BCl / diethyl ether / 0.5 h / 0 °C

9.2: 86 percent / diethyl ether / 20 h / -78 - -30 °C

10.1: 86 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 30 h / -35 - -15 °C

11.1: 94 percent / HCl / CH₂Cl₂; methanol; diethyl ether / 3 h / 25 °C

12.1: 96 percent / TEMPO; PhI(OAc)2 / CH₂Cl₂ / 12 h / 20 °C

13.1: 83 percent / Proton-Sponge(R) / CH₂Cl₂ / 2 h / 0 °C

14.1: DIBAL / CH₂Cl₂ / 2 h / -78 °C

15.1: pyridine; DMAP / CH₂Cl₂ / 12 h / -35 °C

16.1: ZnBr₂ / CH₂Cl₂ / 3.5 h / 0 - 5 °C

17.1: 89 percent / LiAlH(Ot-Bu)3 / tetrahydrofuran / -78 - -10 °C

18.1: 100 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 0 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; Proton-Sponge(R); (1S)-10-camphorsulfonic acid; dicyclohexylboron chloride; mercury(II) diacetate; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; lithium tri-t-butoxyaluminum hydride; triethylamine; zinc dibromide; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; (1S,2R)-1-amino-2-indanol-derived tridentate Cr catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetic acid; acetonitrile; 1.1: hetero-Diels-Alder reaction / 10.1: Evans-Saksena reduction;
DOI:10.1016/S0040-4020(03)00814-7

Reference yield:

: 193416-54-5
(E)-6-(4-methoxybenzyloxy)-1,3-hexen-2-one

: 618096-84-7
Acetic acid (E)-(S)-1-[(2S,5S,6R)-6-((S)-2-methoxy-3-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-propyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-5-methyl-hex-2-enyl ester

Guidance literature:: Multi-step reaction with 19 steps

1.1: 95 percent / Et₃N / diethyl ether / 1.5 h / 0 °C

2.1: 4 Angstroem molecular sieves / (1S,2R)-1-amino-2-indanol-derived tridentate Cr catalyst / 12 h / 20 °C

2.2: 80 percent / conc. HCl / CHCl₃ / 4 h

3.1: NaBH₄ / methanol / 1 h / 20 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

5.1: 10-camphorsulfonic acid / CH₂Cl₂; methanol / 1 h / 20 °C

6.1: pyridine / CH₂Cl₂ / 1 h / -10 °C

7.1: LDA; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C

7.2: tetrahydrofuran; hexane / -78 - 20 °C

8.1: K₂CO₃ / methanol / 12 h / 20 °C

9.1: 86 percent / pyridinium p-toluenesulfonate; Hg(OAc)2; H₂O / tetrahydrofuran / 1.5 h / 45 °C

10.1: Et₃N; c-Hex₂BCl / diethyl ether / 0.5 h / 0 °C

10.2: 86 percent / diethyl ether / 20 h / -78 - -30 °C

11.1: 86 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 30 h / -35 - -15 °C

12.1: 94 percent / HCl / CH₂Cl₂; methanol; diethyl ether / 3 h / 25 °C

13.1: 96 percent / TEMPO; PhI(OAc)2 / CH₂Cl₂ / 12 h / 20 °C

14.1: 83 percent / Proton-Sponge(R) / CH₂Cl₂ / 2 h / 0 °C

15.1: DIBAL / CH₂Cl₂ / 2 h / -78 °C

16.1: pyridine; DMAP / CH₂Cl₂ / 12 h / -35 °C

17.1: ZnBr₂ / CH₂Cl₂ / 3.5 h / 0 - 5 °C

18.1: 89 percent / LiAlH(Ot-Bu)3 / tetrahydrofuran / -78 - -10 °C

19.1: 100 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 0 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; Proton-Sponge(R); (1S)-10-camphorsulfonic acid; dicyclohexylboron chloride; mercury(II) diacetate; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; lithium tri-t-butoxyaluminum hydride; triethylamine; zinc dibromide; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; (1S,2R)-1-amino-2-indanol-derived tridentate Cr catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetic acid; acetonitrile; 2.1: hetero-Diels-Alder reaction / 11.1: Evans-Saksena reduction;
DOI:10.1016/S0040-4020(03)00814-7