(2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-yn-3-ol

Base Information

• Chemical Name: (2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-yn-3-ol
• CAS No.: 333788-71-9
• Molecular Formula: C₃₈H₆₂O₆Si₂
• Molecular Weight: 671.078

Synonyms:(2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-yn-3-ol

Chemical Property of (2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-yn-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-yn-3-ol

There total 12 articles about (2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-yn-3-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: 78.0%

tert-Butyl-[(R)-2-(4-methoxy-benzyloxy)-1-(R)-oxiranyl-ethoxy]-dimethyl-silane (313677-45-1) + [(R)-1-((S)-1-Benzyloxy-propyl)-but-3-ynyloxy]-tert-butyl-dimethyl-silane (333788-69-5) → (2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-yn-3-ol (333788-71-9)

Guidance literature:

With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)02281-4

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threitol (84379-53-3) → (2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-yn-3-ol (333788-71-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / TEA; DMAP / CH₂Cl₂

2: 93 percent / diethyl ether / -65 - 0 °C

3: 97 percent / PPTS / ethanol / 80 °C

4: 100 percent / TEA; DMAP / CH₂Cl₂ / 60 °C

5: 98 percent / TEA; DMAP / CH₂Cl₂

6: 96 percent / TBAF / tetrahydrofuran

7: 93 percent / EDA / dimethylsulfoxide / 0 °C

8: 98 percent / AgNO₃; pyridine / acetonitrile

9: 78 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

With pyridine; diazoacetic acid ethyl ester; dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; silver nitrate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile; 9: Yamaguchi coupling reaction;

DOI:10.1016/S0040-4039(00)02281-4

Reference yield:

(S)-2-(benzyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate (131446-96-3) → (2R,3R,8R,9S)-9-Benzyloxy-2,8-bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-undec-5-yn-3-ol (333788-71-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 93 percent / diethyl ether / -65 - 0 °C

2: 97 percent / PPTS / ethanol / 80 °C

3: 100 percent / TEA; DMAP / CH₂Cl₂ / 60 °C

4: 98 percent / TEA; DMAP / CH₂Cl₂

5: 96 percent / TBAF / tetrahydrofuran

6: 93 percent / EDA / dimethylsulfoxide / 0 °C

7: 98 percent / AgNO₃; pyridine / acetonitrile

8: 78 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

With pyridine; diazoacetic acid ethyl ester; dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; silver nitrate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile; 8: Yamaguchi coupling reaction;

DOI:10.1016/S0040-4039(00)02281-4

upstream raw materials:

tert-Butyl-[(R)-2-(4-methoxy-benzyloxy)-1-(R)-oxiranyl-ethoxy]-dimethyl-silane

[(R)-1-((S)-1-Benzyloxy-propyl)-but-3-ynyloxy]-tert-butyl-dimethyl-silane

2-O-benzyl-3,4-O-isopropylidene-L-threitol

(S)-2-(benzyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

Downstream raw materials:

(2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-(S)-oxiranyl-2,3,6,7-tetrahydro-oxepine

(2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-((Z)-(R)-1-chloro-hex-3-en-5-ynyl)-2,3,6,7-tetrahydro-oxepine

Methanesulfonic acid (R)-1-[(2R,7R)-7-((S)-1-benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-2-hydroxy-ethyl ester

(Z)-(S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-hex-3-en-5-yn-1-ol

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