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}-ethanol

Base Information

• Chemical Name: 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}-ethanol
• CAS No.: 627511-98-2
• Molecular Formula: C₃₄H₆₂O₇Si₂
• Molecular Weight: 639.033

Synonyms: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}-ethanol

Chemical Property of 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}-ethanol

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Technology Process of 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}-ethanol

There total 10 articles about 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}-ethanol 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: 86.0%

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 (627511-97-1) → 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}-ethanol (627511-98-2)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃;

DOI:10.1016/j.tetlet.2003.08.082

Reference yield:

(S)-2-((S)-2-Benzyloxy-4-trityloxy-butyl)-oxirane (209340-30-7) → 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}-ethanol (627511-98-2)

Guidance literature:

Multi-step reaction with 10 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

9: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

10: 86 percent / DIBALH / CH₂Cl₂; hexane / -78 °C

With 2,6-dimethylpyridine; 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

Reference yield:

tert-Butyl-[(S)-1-[1,3]dithian-2-ylmethyl-1-methyl-2-((R)-2-phenyl-[1,3]dioxan-4-yl)-ethoxy]-dimethyl-silane → 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}-ethanol (627511-98-2)

Guidance literature:

Multi-step reaction with 10 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

9: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

10: 86 percent / DIBALH / CH₂Cl₂; hexane / -78 °C

With 2,6-dimethylpyridine; 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:

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

triethylsilyl trifluoroacetate

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

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

Downstream raw materials:

{(2R,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}-acetaldehyde

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

Acetic acid (2S,4S,6R,8R,10S)-2-[2-(4-methoxy-benzyloxy)-ethyl]-10-methyl-10-triethylsilanyloxy-8-((Z)-2-trimethylsilanyloxy-but-2-enyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

1-{(2R,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}-butan-2-one

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