[(2R,3S,6R,8R,9S)-9-Methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-acetaldehyde

Base Information

• Chemical Name: [(2R,3S,6R,8R,9S)-9-Methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-acetaldehyde
• CAS No.: 902453-72-9
• Molecular Formula: C₂₂H₃₀O₆
• Molecular Weight: 390.477

Synonyms:[(2R,3S,6R,8R,9S)-9-Methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-acetaldehyde

Chemical Property of [(2R,3S,6R,8R,9S)-9-Methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3S,6R,8R,9S)-9-Methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-acetaldehyde

There total 12 articles about [(2R,3S,6R,8R,9S)-9-Methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-acetaldehyde 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%

2-[(2R,3S,6R,8R,9S)-9-Methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-ethanol (902453-81-0) → [(2R,3S,6R,8R,9S)-9-Methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-acetaldehyde (902453-72-9)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1055/s-2006-933144

Reference yield:

(2R,3S)-3-Methoxy-1-(4-methoxy-benzyloxy)-pent-4-en-2-ol (902453-84-3) → [(2R,3S,6R,8R,9S)-9-Methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-acetaldehyde (902453-72-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: imidazole / dimethylformamide

2.1: 73 percent / Ru(Co)12

3.1: 92 percent / i-PrMgCl / HCl; tetrahydrofuran

4.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 20 °C

4.2: 82 percent / tetrahydrofuran; hexane / 1.5 h / 20 °C

5.1: 85 percent / quinoline; H₂ / Lindlar catalyst

6.1: 91 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O

7.1: 78 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

With 1H-imidazole; quinoline; n-butyllithium; oxalyl dichloride; hydrogen; isopropylmagnesium chloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; Lindlar's catalyst; Ru(CO)12; In tetrahydrofuran; hydrogenchloride; hexane; dichloromethane; water; N,N-dimethyl-formamide; 7.1: Swern oxidation;

DOI:10.1055/s-2006-933144

Reference yield:

Triethyl-[(1R,2S)-2-methoxy-1-(4-methoxy-benzyloxymethyl)-but-3-enyloxy]-silane (902453-78-5) → [(2R,3S,6R,8R,9S)-9-Methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-acetaldehyde (902453-72-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 73 percent / Ru(Co)12

2.1: 92 percent / i-PrMgCl / HCl; tetrahydrofuran

3.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 20 °C

3.2: 82 percent / tetrahydrofuran; hexane / 1.5 h / 20 °C

4.1: 85 percent / quinoline; H₂ / Lindlar catalyst

5.1: 91 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O

6.1: 78 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

With quinoline; n-butyllithium; oxalyl dichloride; hydrogen; isopropylmagnesium chloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; Lindlar's catalyst; Ru(CO)12; In tetrahydrofuran; hydrogenchloride; hexane; dichloromethane; water; 6.1: Swern oxidation;

DOI:10.1055/s-2006-933144

upstream raw materials:

2-[(2R,3S,6R,8R,9S)-9-Methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-ethanol

(2R,3S)-3-Methoxy-1-(4-methoxy-benzyloxy)-pent-4-en-2-ol

Triethyl-[(1R,2S)-2-methoxy-1-(4-methoxy-benzyloxymethyl)-but-3-enyloxy]-silane

(4S,5R)-4-Methoxy-6-(4-methoxy-benzyloxy)-5-triethylsilanyloxy-hexanoic acid methoxy-methyl-amide

Downstream raw materials:

((2S,6R)-6-{(R)-4-Hydroxy-5-[(2R,3S,6R,8R,9S)-9-methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-2-oxo-pentyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester

((2R,6S)-6-{(R)-4-Hydroxy-5-[(2R,3S,6R,8R,9S)-9-methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-2-oxo-pentyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester

((2S,6R)-6-{(2S,4S)-2,4-Dihydroxy-5-[(2R,3S,6R,8R,9S)-9-methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-pentyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester

((2R,6S)-6-{(2S,4S)-2,4-Dihydroxy-5-[(2R,3S,6R,8R,9S)-9-methoxy-8-(4-methoxy-benzyloxymethyl)-3-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-pentyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester

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