(2S,4R,6S)-1-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-6-(tert-butyl-diphenyl-silanyloxy)-non-8-ene-2,4-diol

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Chemical Name:(2S,4R,6S)-1-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-6-(tert-butyl-diphenyl-silanyloxy)-non-8-ene-2,4-diol
CAS No.:321667-17-8
Molecular Formula:C₃₄H₅₀O₄Si
Molecular Weight:550.854
Hs Code.:

Synonyms:(2S,4R,6S)-1-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-6-(tert-butyl-diphenyl-silanyloxy)-non-8-ene-2,4-diol

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Chemical Property of (2S,4R,6S)-1-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-6-(tert-butyl-diphenyl-silanyloxy)-non-8-ene-2,4-diol

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Technology Process of (2S,4R,6S)-1-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-6-(tert-butyl-diphenyl-silanyloxy)-non-8-ene-2,4-diol

There total 10 articles about (2S,4R,6S)-1-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-6-(tert-butyl-diphenyl-silanyloxy)-non-8-ene-2,4-diol 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: 98.0%

: 321667-15-6
{(S)-1-[(4R,6S)-6-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-but-3-enyloxy}-tert-butyl-diphenyl-silane

: 321667-17-8
(2S,4R,6S)-1-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-6-(tert-butyl-diphenyl-silanyloxy)-non-8-ene-2,4-diol

Guidance literature:: With acetic acid; at 40 ℃; for 2h;
DOI:10.1021/ja003593m

Reference yield:

: 127793-65-1
(3R)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-ol

: 321667-17-8
(2S,4R,6S)-1-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-6-(tert-butyl-diphenyl-silanyloxy)-non-8-ene-2,4-diol

Guidance literature:: Multi-step reaction with 10 steps

1.1: HgClOAc; Yb(OTf)3 / 1.5 h / 20 °C

1.2: 1.96 g / H₂; DABCO; P(O-o-t-BuPh)3 / Rh(acac)(CO)2 / ethyl acetate / 26 h / 50 °C / 41372.9 Torr

2.1: BF₃*Et₂O / tetrahydrofuran / 3 h / -78 °C

2.2: 67 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 16 h / 20 °C

3.1: 89 percent / PPh₃; H₂ / Rh(acac)(CO)2 / tetrahydrofuran / 48 h / 50 °C / 20686.5 Torr

4.1: DMAP; pyridine / CH₂Cl₂ / 17 h / 20 °C

5.1: Ti(O-i-Pr)2Cl₂; TiCl₄ / CH₂Cl₂ / 1 h / -78 °C

6.1: 1.93 g / n-Bu₄F / tetrahydrofuran / 3 h / 20 °C

7.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 40 °C

8.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1.25 h / -78 - 20 °C

8.2: diethyl ether / 2 h / -78 - 20 °C

8.3: 2.92 g / aq. H₂O₂; aq. NaOH / diethyl ether / 16 h

9.1: 99 percent / imidazole / dimethylformamide / 3 h

10.1: 98 percent / aq. AcOH / 2 h / 40 °C

With pyridine; (-)-B-methoxydiisopinocamphenylborane; 1H-imidazole; dmap; titanium(IV) dichlorodiisopropylate; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; titanium tetrachloride; chloro(acetato)mercury(II); acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; ytterbium(III) triflate; acetylacetonatodicarbonylrhodium(l); In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 7.1: Swern oxidation;
DOI:10.1021/ja003593m

Reference yield:

: 321667-01-0
{(4S,6S)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetaldehyde

: 321667-17-8
(2S,4R,6S)-1-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-6-(tert-butyl-diphenyl-silanyloxy)-non-8-ene-2,4-diol

Guidance literature:: Multi-step reaction with 9 steps

1.1: BF₃*Et₂O / tetrahydrofuran / 3 h / -78 °C

1.2: 67 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 16 h / 20 °C

2.1: 89 percent / PPh₃; H₂ / Rh(acac)(CO)2 / tetrahydrofuran / 48 h / 50 °C / 20686.5 Torr

3.1: DMAP; pyridine / CH₂Cl₂ / 17 h / 20 °C

4.1: Ti(O-i-Pr)2Cl₂; TiCl₄ / CH₂Cl₂ / 1 h / -78 °C

5.1: 1.93 g / n-Bu₄F / tetrahydrofuran / 3 h / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 40 °C

7.1: (-)-B-methoxydiisopinocampheylborane / diethyl ether / 1.25 h / -78 - 20 °C

7.2: diethyl ether / 2 h / -78 - 20 °C

7.3: 2.92 g / aq. H₂O₂; aq. NaOH / diethyl ether / 16 h

8.1: 99 percent / imidazole / dimethylformamide / 3 h

9.1: 98 percent / aq. AcOH / 2 h / 40 °C

With pyridine; (-)-B-methoxydiisopinocamphenylborane; 1H-imidazole; dmap; titanium(IV) dichlorodiisopropylate; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; titanium tetrachloride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; acetylacetonatodicarbonylrhodium(l); In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 6.1: Swern oxidation;
DOI:10.1021/ja003593m