2,2-dimethyl-propionic acid 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyl ester

Base Information

• Chemical Name: 2,2-dimethyl-propionic acid 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyl ester
• CAS No.: 676474-16-1
• Molecular Formula: C₃₃H₅₂O₆Si
• Molecular Weight: 572.858

Synonyms:2,2-dimethyl-propionic acid 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyl ester

Chemical Property of 2,2-dimethyl-propionic acid 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 2,2-dimethyl-propionic acid 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyl ester

There total 9 articles about 2,2-dimethyl-propionic acid 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyl ester 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: 90.0%

t-butyldimethylsiyl triflate (69739-34-0) + 2,2-dimethyl-propionic acid 6-hydroxy-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyl ester (676473-77-1) → 2,2-dimethyl-propionic acid 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyl ester (676474-16-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1016/j.bmcl.2003.12.001

Reference yield:

2-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose (152453-72-0) → 2,2-dimethyl-propionic acid 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyl ester (676474-16-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: NaH / tetrahydrofuran / 0 °C

1.2: 85 percent / Bu₃P / acetonitrile / 60 °C

2.1: DIBAL / CH₂Cl₂ / -78 °C

3.1: 85 percent / pyridine / CH₂Cl₂

4.1: aq. HCl / tetrahydrofuran

5.1: NaIO₄ / tetrahydrofuran; H₂O / 0 °C

6.1: NaClO₂; H₂NSO₃H / 2-methyl-propan-2-ol; H₂O / 0 °C

7.1: 50 percent / methanol; toluene

8.1: tetrahydrofuran / -78 °C

9.1: pyridine / CH₂Cl₂

10.1: 70 percent / Et₃N; LiCl / tetrahydrofuran / 0 - 20 °C

11.1: 70 percent / L-selectride / tetrahydrofuran / -78 °C

12.1: 90 percent / imidazole / dimethylformamide / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium chlorite; sodium periodate; aminosulfonic acid; L-Selectride; sodium hydride; diisobutylaluminium hydride; triethylamine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.bmcl.2003.12.001

Reference yield:

5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester (676474-12-7) → 2,2-dimethyl-propionic acid 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyl ester (676474-16-1)

Guidance literature:

Multi-step reaction with 11 steps

1: DIBAL / CH₂Cl₂ / -78 °C

2: 85 percent / pyridine / CH₂Cl₂

3: aq. HCl / tetrahydrofuran

4: NaIO₄ / tetrahydrofuran; H₂O / 0 °C

5: NaClO₂; H₂NSO₃H / 2-methyl-propan-2-ol; H₂O / 0 °C

6: 50 percent / methanol; toluene

7: tetrahydrofuran / -78 °C

8: pyridine / CH₂Cl₂

9: 70 percent / Et₃N; LiCl / tetrahydrofuran / 0 - 20 °C

10: 70 percent / L-selectride / tetrahydrofuran / -78 °C

11: 90 percent / imidazole / dimethylformamide / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium chlorite; sodium periodate; aminosulfonic acid; L-Selectride; diisobutylaluminium hydride; triethylamine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2003.12.001

upstream raw materials:

t-butyldimethylsiyl triflate

2,2-dimethyl-propionic acid 6-hydroxy-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyl ester

2-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose

5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-pent-2-enoic acid methyl ester

Downstream raw materials:

laulimalide

(2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal

11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-dien-6-ol

6,11-bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-1-(6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-trideca-7,12-diene

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