tert-Butyl-(5-{(4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pent-3-ynyloxy)-dimethyl-silane

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Chemical Name:tert-Butyl-(5-{(4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pent-3-ynyloxy)-dimethyl-silane
CAS No.:329708-78-3
Molecular Formula:C₂₉H₄₈O₅Si
Molecular Weight:504.783
Hs Code.:

Synonyms:tert-Butyl-(5-{(4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pent-3-ynyloxy)-dimethyl-silane

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Chemical Property of tert-Butyl-(5-{(4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pent-3-ynyloxy)-dimethyl-silane

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Technology Process of tert-Butyl-(5-{(4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pent-3-ynyloxy)-dimethyl-silane

There total 16 articles about tert-Butyl-(5-{(4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pent-3-ynyloxy)-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:

: 78592-82-2
4-(tert-butyldimethylsilyloxy)-1-butyne

: Trifluoro-methanesulfonic acid (4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

: 329708-78-3
tert-Butyl-(5-{(4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pent-3-ynyloxy)-dimethyl-silane

Guidance literature:: 4-(tert-butyldimethylsilyloxy)-1-butyne; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -78 - -35 ℃;

Trifluoro-methanesulfonic acid (4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester; In tetrahydrofuran; hexane; at -35 - 20 ℃; for 5h;
DOI:10.1016/S0040-4020(02)00056-X

Reference yield:

: 73346-74-4
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

: 329708-78-3
tert-Butyl-(5-{(4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pent-3-ynyloxy)-dimethyl-silane

Guidance literature:: Multi-step reaction with 14 steps

1.1: 97 percent / NaH / 1,2-dimethoxy-ethane / 0 - 20 °C

2.1: (COCl)2; DMSO, Et₃N / CH₂Cl₂ / -78 - 0 °C

3.1: CuI / diethyl ether / -78 - 0 °C

4.1: 96 percent / (COCl)2; DMSO; Et₃N / -78 - 0 °C

5.1: 95 percent / BuLi / -40 - 0 °C

6.1: 9-BBN / tetrahydrofuran / 16 h / 0 - 20 °C

6.2: hydrogen peroxide; aq. sodium acetate / ethanol / 6 h / 0 - 20 °C

7.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

8.1: 84 percent / t-BuOK / tetrahydrofuran / -78 - 0 °C

9.1: 87 percent / H₂ / Rh-Al₂O₃ / ethyl acetate / 20 °C

10.1: DIBAL / CH₂Cl₂ / -78 °C

10.2: 90 percent / NaBH₄ / ethanol / 0 °C

11.1: 82 percent / NaH / dimethylformamide / -20 °C

12.1: 99 percent / Bu₄NF / tetrahydrofuran / 20 °C

13.1: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0.67 h / -10 °C

14.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 0.67 h / -78 - -35 °C

14.2: 18.8 mg / tetrahydrofuran; hexane / -35 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; rhodium on alumina; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 2.1: Swern oxidation / 5.1: Wittig reaction / 8.1: Horner-Emmons reaction;
DOI:10.1021/ol006905z

Reference yield:

: 125993-65-9
(4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

: 329708-78-3
tert-Butyl-(5-{(4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pent-3-ynyloxy)-dimethyl-silane

Guidance literature:: Multi-step reaction with 12 steps

1.1: CuI / diethyl ether / -78 - 0 °C

2.1: 96 percent / (COCl)2; DMSO; Et₃N / -78 - 0 °C

3.1: 95 percent / BuLi / -40 - 0 °C

4.1: 9-BBN / tetrahydrofuran / 16 h / 0 - 20 °C

4.2: hydrogen peroxide; aq. sodium acetate / ethanol / 6 h / 0 - 20 °C

5.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

6.1: 84 percent / t-BuOK / tetrahydrofuran / -78 - 0 °C

7.1: 87 percent / H₂ / Rh-Al₂O₃ / ethyl acetate / 20 °C

8.1: DIBAL / CH₂Cl₂ / -78 °C

8.2: 90 percent / NaBH₄ / ethanol / 0 °C

9.1: 82 percent / NaH / dimethylformamide / -20 °C

10.1: 99 percent / Bu₄NF / tetrahydrofuran / 20 °C

11.1: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0.67 h / -10 °C

12.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 0.67 h / -78 - -35 °C

12.2: 18.8 mg / tetrahydrofuran; hexane / -35 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; rhodium on alumina; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3.1: Wittig reaction / 6.1: Horner-Emmons reaction;
DOI:10.1021/ol006905z