2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol

Base Information

• Chemical Name: 2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol
• CAS No.: 890027-63-1
• Molecular Formula: C₃₂H₄₈O₅Si
• Molecular Weight: 540.816
• Mol file: 890027-63-1.mol

Synonyms:2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol

Chemical Property of 2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol

There total 31 articles about 2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-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: 100.0%

(-)-tert-butyl-[(2R,4S,5S,6R,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-vinyl-1-oxaspiro[4.4]non-2-ylmethoxy]diphenylsilane (890027-31-3) → 2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol (890027-63-1)

Guidance literature:

(-)-tert-butyl-[(2R,4S,5S,6R,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-vinyl-1-oxaspiro[4.4]non-2-ylmethoxy]diphenylsilane; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201104447

Reference yield:

(R)-acetic acid 4-hydroxy-2-methoxymethoxymethyl-2-methylbutyl ester (890027-50-6) → 2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol (890027-63-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 96 percent / PPTS / CH₂Cl₂ / 20 °C

2.1: 99 percent / K₂CO₃ / methanol / 20 °C

3.1: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: t-BuOK / tetrahydrofuran / 0.17 h / 0 °C

4.2: 100 percent / tetrahydrofuran / -78 - 20 °C

5.1: 100 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6.1: 96 percent / 2,6-lutidine; MsCl; LiCl / dimethylformamide / 0 °C

7.1: 86 percent / HMPA; MeLi / diethyl ether / -65 °C

8.1: 100 percent / PPTs / ethanol / 20 °C

9.1: 92 percent / imidazole; I₂ / benzene / 20 °C

10.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

10.2: 84 percent / diethyl ether; pentane

11.1: 29 percent / TiCl₃(Oi-Pr) / CH₂Cl₂ / 4 h / -78 °C

12.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

12.2: 99 percent / NaOH; H₂O₂ / tetrahydrofuran / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; titanium(IV) trichloride isopropoxide; potassium tert-butylate; methyllithium; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; pentane; benzene; 3.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/ol060437x

Reference yield:

4-isopropyl-3-(2-methyl-pent-4-enoyl)-oxazolidin-2-one → 2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol (890027-63-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 92 percent / NCS; NaHCO₃; NaI / ethyl acetate; H₂O / 20 °C

2.1: CF₃COONa / dimethylformamide / 90 °C

2.2: 63 percent / diethylamine / dimethylformamide / 20 °C

3.1: 97 percent / imidazole / CH₂Cl₂ / 20 °C

4.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

4.2: 84 percent / diethyl ether; pentane

5.1: 29 percent / TiCl₃(Oi-Pr) / CH₂Cl₂ / 4 h / -78 °C

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

6.2: 99 percent / NaOH; H₂O₂ / tetrahydrofuran / 20 °C

With 1H-imidazole; N-chloro-succinimide; 9-borabicyclo[3.3.1]nonane dimer; titanium(IV) trichloride isopropoxide; tert.-butyl lithium; sodium 2,2,2-trifluoroacetate; sodium hydrogencarbonate; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; pentane;

DOI:10.1021/ol060437x

upstream raw materials:

(-)-tert-butyl-[(2R,4S,5S,6R,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-vinyl-1-oxaspiro[4.4]non-2-ylmethoxy]diphenylsilane

(R)-acetic acid 4-hydroxy-2-methoxymethoxymethyl-2-methylbutyl ester

(E)-(R)-2-hydroxymethyl-2-methyl-5-phenylpent-4-enoic acid methyl ester

(R)-2-methyl-2-(3-phenyl-2-propenyl)malonic acid monomethyl ester

Downstream raw materials:

(-)-3,5-dinitro-benzoic acid (2R,4S,5S,6R,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-(2-oxoethyl)-1-oxaspiro[4.4]non-2-ylmethyl ester

(-)-3,5-dinitro-benzoic acid (2R,4S,5S,6R,7S)-6-(2-hydroxyethyl)-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-2-ylmethyl ester

2-{(2R,4S,5S,6R,7S)-2-tert-butyldiphenylsilyloxymethyl-7-methoxymethoxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl}ethyl pivalate

Ophiobolin A

Refernces

• 1、 Tsuna, Kazuhiro,Noguchi, Naoyoshi,Nakada, Masahisa. "Convergent total synthesis of (+)-ophiobolin A". supporting information; experimental part. p. 9452 - 9455. Retrieved 2011/11/06.