(2R,3S,5R,8R)-5-(tert-butyldimethylsilyloxy)-8-(4-methoxyphenylmethoxymethyl)-2-[(2E)-5-trimethylsilylpent-2-en-4-ynyl]-oxocan-3-ol

Base Information

Chemical Name:(2R,3S,5R,8R)-5-(tert-butyldimethylsilyloxy)-8-(4-methoxyphenylmethoxymethyl)-2-[(2E)-5-trimethylsilylpent-2-en-4-ynyl]-oxocan-3-ol
CAS No.:477198-71-3
Molecular Formula:C₃₀H₅₀O₅Si₂
Molecular Weight:546.895
Hs Code.:

Synonyms:(2R,3S,5R,8R)-5-(tert-butyldimethylsilyloxy)-8-(4-methoxyphenylmethoxymethyl)-2-[(2E)-5-trimethylsilylpent-2-en-4-ynyl]-oxocan-3-ol

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Chemical Property of (2R,3S,5R,8R)-5-(tert-butyldimethylsilyloxy)-8-(4-methoxyphenylmethoxymethyl)-2-[(2E)-5-trimethylsilylpent-2-en-4-ynyl]-oxocan-3-ol

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Technology Process of (2R,3S,5R,8R)-5-(tert-butyldimethylsilyloxy)-8-(4-methoxyphenylmethoxymethyl)-2-[(2E)-5-trimethylsilylpent-2-en-4-ynyl]-oxocan-3-ol

There total 14 articles about (2R,3S,5R,8R)-5-(tert-butyldimethylsilyloxy)-8-(4-methoxyphenylmethoxymethyl)-2-[(2E)-5-trimethylsilylpent-2-en-4-ynyl]-oxocan-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: 78.0%

: 42134-49-6
(3-trimethylsilyl-2-propynyl)triphenylphosphonium bromide

: (3aR,5R,8R,9aS)-8-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-octahydro-furo[3,2-b]oxocin-2-ol

: (2R,3S,5R,8R)-5-(tert-Butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxymethyl)-2-((Z)-5-trimethylsilanyl-pent-2-en-4-ynyl)-oxocan-3-ol

: 477198-71-3
(2R,3S,5R,8R)-5-(tert-butyldimethylsilyloxy)-8-(4-methoxyphenylmethoxymethyl)-2-[(2E)-5-trimethylsilylpent-2-en-4-ynyl]-oxocan-3-ol

Guidance literature:: (3-trimethylsilyl-2-propynyl)triphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -40 ℃; for 0.5h;

(3aR,5R,8R,9aS)-8-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-octahydro-furo[3,2-b]oxocin-2-ol; In tetrahydrofuran; hexane; at 0 ℃; for 4h; Further stages.;
DOI:10.1021/ol0267174

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 477198-71-3
(2R,3S,5R,8R)-5-(tert-butyldimethylsilyloxy)-8-(4-methoxyphenylmethoxymethyl)-2-[(2E)-5-trimethylsilylpent-2-en-4-ynyl]-oxocan-3-ol

Guidance literature:: Multi-step reaction with 13 steps

1.1: 19.76 g / pyridine / 2 h / 0 °C

2.1: 93 percent / NaH / dimethylformamide / 40 h / Heating

3.1: 95 percent / H₂ / Pd/C / ethyl acetate / 48 h / 2585.81 Torr

4.1: 90 percent / CHCl₃ / 7 h / Heating

5.1: BH₃*S(CH₃)2 / (S)-2-Me-4,4-Ph₂-1-aza-2-bora-3-oxabicyclo[3.3.0]octan / CH₂Cl₂ / 13.5 h / -20 °C

6.1: 14.53 g / pyridine / DMAP / tetrahydrofuran / 2 h / 20 °C

7.1: 75 percent / NaH / toluene / 0.5 h / 120 °C

8.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C

9.1: 5 percent Spectr_. / Dess-Martin periodinane; polyvinyl pyridine / CH₂Cl₂ / 1 h / 20 °C

10.1: 91 percent / H₂ / RhCl(PPh₃)3 / toluene / 30 h / 2327.23 Torr

11.1: 90 percent / [RhClCOD]2 / 1,3-bis-(diphenylphosphino)-propane / xylene / 96 h / Heating

12.1: dimethyldioxirane / CH₂Cl₂; acetone / -78 °C

12.2: LDA / tetrahydrofuran / -78 - -25 °C

12.3: 91 percent / HIO₄; sodium acetate / acetic acid; tetrahydrofuran; H₂O / 3 h / 20 °C

13.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -40 °C

13.2: 78 percent / tetrahydrofuran; hexane / 4 h / 0 °C

With pyridine; lithium aluminium tetrahydride; n-butyllithium; polyvinyl pyridine; dimethylsulfide borane complex; hydrogen; 3,3-dimethyldioxirane; sodium hydride; Dess-Martin periodane; dmap; palladium on activated charcoal; RhCl(PPh₃)3; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; xylene; 13.1: Wittig olefination;
DOI:10.1021/ol0267174

Reference yield:

: 173613-40-6
1-(4-methoxyphenylmethoxy)-3-(triphenylphosphanylidene)-propan-2-one

: 477198-71-3
(2R,3S,5R,8R)-5-(tert-butyldimethylsilyloxy)-8-(4-methoxyphenylmethoxymethyl)-2-[(2E)-5-trimethylsilylpent-2-en-4-ynyl]-oxocan-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 90 percent / CHCl₃ / 7 h / Heating

2.1: BH₃*S(CH₃)2 / (S)-2-Me-4,4-Ph₂-1-aza-2-bora-3-oxabicyclo[3.3.0]octan / CH₂Cl₂ / 13.5 h / -20 °C

3.1: 14.53 g / pyridine / DMAP / tetrahydrofuran / 2 h / 20 °C

4.1: 75 percent / NaH / toluene / 0.5 h / 120 °C

5.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C

6.1: 5 percent Spectr_. / Dess-Martin periodinane; polyvinyl pyridine / CH₂Cl₂ / 1 h / 20 °C

7.1: 91 percent / H₂ / RhCl(PPh₃)3 / toluene / 30 h / 2327.23 Torr

8.1: 90 percent / [RhClCOD]2 / 1,3-bis-(diphenylphosphino)-propane / xylene / 96 h / Heating

9.1: dimethyldioxirane / CH₂Cl₂; acetone / -78 °C

9.2: LDA / tetrahydrofuran / -78 - -25 °C

9.3: 91 percent / HIO₄; sodium acetate / acetic acid; tetrahydrofuran; H₂O / 3 h / 20 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -40 °C

10.2: 78 percent / tetrahydrofuran; hexane / 4 h / 0 °C

With pyridine; lithium aluminium tetrahydride; n-butyllithium; polyvinyl pyridine; dimethylsulfide borane complex; hydrogen; 3,3-dimethyldioxirane; sodium hydride; Dess-Martin periodane; dmap; RhCl(PPh₃)3; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; chloroform; acetone; toluene; xylene; 10.1: Wittig olefination;
DOI:10.1021/ol0267174