2,2-Dimethyl-propionic acid 2-{(2S,4S,6R,8S,10S)-4,10-dihydroxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-1,7-dioxa-spiro[5.5]undec-2-yl}-ethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid 2-{(2S,4S,6R,8S,10S)-4,10-dihydroxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-1,7-dioxa-spiro[5.5]undec-2-yl}-ethyl ester
• CAS No.: 627511-96-0
• Molecular Formula: C₂₇H₄₂O₈
• Molecular Weight: 494.626

Synonyms:2,2-Dimethyl-propionic acid 2-{(2S,4S,6R,8S,10S)-4,10-dihydroxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-1,7-dioxa-spiro[5.5]undec-2-yl}-ethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid 2-{(2S,4S,6R,8S,10S)-4,10-dihydroxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-1,7-dioxa-spiro[5.5]undec-2-yl}-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid 2-{(2S,4S,6R,8S,10S)-4,10-dihydroxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-1,7-dioxa-spiro[5.5]undec-2-yl}-ethyl ester

There total 9 articles about 2,2-Dimethyl-propionic acid 2-{(2S,4S,6R,8S,10S)-4,10-dihydroxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-1,7-dioxa-spiro[5.5]undec-2-yl}-ethyl 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: 54.0%

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) + 2,2-Dimethyl-propionic acid 2-[(2S,4S,6R,8S,10S)-4,10-dihydroxy-8-(2-hydroxy-ethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethyl ester (627511-84-6) → 2,2-Dimethyl-propionic acid 2-{(2S,4S,6R,8S,10S)-4,10-dihydroxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-1,7-dioxa-spiro[5.5]undec-2-yl}-ethyl ester (627511-96-0)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2003.08.082

Reference yield:

pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid 2-{(2S,4S,6R,8S,10S)-4,10-dihydroxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-1,7-dioxa-spiro[5.5]undec-2-yl}-ethyl ester (627511-96-0)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂ / 20 °C

2: Hg(ClO₄)2; CaCO₃ / tetrahydrofuran; H₂O / 0 °C

3: 89 percent / aq. HF / acetonitrile / 40 °C

4: H₂ / Pd/C / ethyl acetate / 20 °C

5: PPTS / CH₂Cl₂ / 20 °C

6: 54 percent / PPTS / CH₂Cl₂ / 20 °C

With mercury(II) perchlorate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; triethylamine; calcium carbonate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/j.tetlet.2003.08.082

Reference yield:

(S)-2-((S)-2-Benzyloxy-4-trityloxy-butyl)-oxirane (209340-30-7) → 2,2-Dimethyl-propionic acid 2-{(2S,4S,6R,8S,10S)-4,10-dihydroxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-1,7-dioxa-spiro[5.5]undec-2-yl}-ethyl ester (627511-96-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / n-BuLi; HMPA / tetrahydrofuran / -20 °C

2: DIBALH / CH₂Cl₂; hexane / 20 °C

3: Et₃N / CH₂Cl₂ / 20 °C

4: Hg(ClO₄)2; CaCO₃ / tetrahydrofuran; H₂O / 0 °C

5: 89 percent / aq. HF / acetonitrile / 40 °C

6: H₂ / Pd/C / ethyl acetate / 20 °C

7: PPTS / CH₂Cl₂ / 20 °C

8: 54 percent / PPTS / CH₂Cl₂ / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; mercury(II) perchlorate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; calcium carbonate; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1016/j.tetlet.2003.08.082

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

2,2-Dimethyl-propionic acid 2-[(2S,4S,6R,8S,10S)-4,10-dihydroxy-8-(2-hydroxy-ethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-ethyl ester

pivaloyl chloride

(S)-2-((S)-2-Benzyloxy-4-trityloxy-butyl)-oxirane

Downstream raw materials:

2,2-Dimethyl-propionic acid 2-{(2S,4S,6R,8S,10S)-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-4,10-bis-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl}-ethyl ester

3,3,3-trifluoro-2-methoxy-2-phenyl-propionic acid 1-(3-{10-acetoxy-8-[2-(4-methoxy-benzyloxy)-ethyl]-4-methyl-4-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-2-yl}-1-methyl-2-oxo-propyl)-3-(4-methoxy-benzyloxy)-2-methyl-pentyl ester

Acetic acid (2S,4S,6R,8R,10S)-8-[(3S,4R,5S,6S)-4-hydroxy-6-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-octyl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester

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