(5S,7R,9R,10R,11R,12S)-5-(benzyloxymethyl)-7,9-bis(tert-butyldimethylsilyloxy)-15,15-diethyl-11-(4-methoxybenzyloxy)-2,2,3,3,10,12-hexamethyl-4,14-dioxa-3,15-disilaheptadecane

Base Information

• Chemical Name: (5S,7R,9R,10R,11R,12S)-5-(benzyloxymethyl)-7,9-bis(tert-butyldimethylsilyloxy)-15,15-diethyl-11-(4-methoxybenzyloxy)-2,2,3,3,10,12-hexamethyl-4,14-dioxa-3,15-disilaheptadecane
• CAS No.: 929883-06-7
• Molecular Formula: C₅₁H₉₆O₇Si₄
• Molecular Weight: 933.661

Synonyms:(5S,7R,9R,10R,11R,12S)-5-(benzyloxymethyl)-7,9-bis(tert-butyldimethylsilyloxy)-15,15-diethyl-11-(4-methoxybenzyloxy)-2,2,3,3,10,12-hexamethyl-4,14-dioxa-3,15-disilaheptadecane

Chemical Property of (5S,7R,9R,10R,11R,12S)-5-(benzyloxymethyl)-7,9-bis(tert-butyldimethylsilyloxy)-15,15-diethyl-11-(4-methoxybenzyloxy)-2,2,3,3,10,12-hexamethyl-4,14-dioxa-3,15-disilaheptadecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,7R,9R,10R,11R,12S)-5-(benzyloxymethyl)-7,9-bis(tert-butyldimethylsilyloxy)-15,15-diethyl-11-(4-methoxybenzyloxy)-2,2,3,3,10,12-hexamethyl-4,14-dioxa-3,15-disilaheptadecane

There total 7 articles about (5S,7R,9R,10R,11R,12S)-5-(benzyloxymethyl)-7,9-bis(tert-butyldimethylsilyloxy)-15,15-diethyl-11-(4-methoxybenzyloxy)-2,2,3,3,10,12-hexamethyl-4,14-dioxa-3,15-disilaheptadecane 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: 92.0%

(2S,3R,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyldecan-1-ol (929882-84-8) + triethylsilyl trifluoromethyl sulfonate (79271-56-0) → (5S,7R,9R,10R,11R,12S)-5-(benzyloxymethyl)-7,9-bis(tert-butyldimethylsilyloxy)-15,15-diethyl-11-(4-methoxybenzyloxy)-2,2,3,3,10,12-hexamethyl-4,14-dioxa-3,15-disilaheptadecane (929883-06-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; for 0.416667h;

DOI:10.1002/anie.200603654

Reference yield:

(R)-3-((2R,3S,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one (929882-93-9) → (5S,7R,9R,10R,11R,12S)-5-(benzyloxymethyl)-7,9-bis(tert-butyldimethylsilyloxy)-15,15-diethyl-11-(4-methoxybenzyloxy)-2,2,3,3,10,12-hexamethyl-4,14-dioxa-3,15-disilaheptadecane (929883-06-7)

Guidance literature:

Multi-step reaction with 4 steps

1: lithium borohydride / diethyl ether; H₂O / 1 h / 0 °C

2: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h / 20 °C

3: 91 percent / BH₃*THF; Sc(OTf)3 / CH₂Cl₂; tetrahydrofuran / 1 h

4: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h

With 2,6-dimethylpyridine; lithium borohydride; borane-THF; pyridinium p-toluenesulfonate; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1002/anie.200603654

Reference yield:

(R)-3-((2R,3S,4S,5R,7R,9S)-10-(benzyloxy)-7,9-bis(tert-butyldimethylsilyloxy)-3,5-dihydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one (929882-83-7) → (5S,7R,9R,10R,11R,12S)-5-(benzyloxymethyl)-7,9-bis(tert-butyldimethylsilyloxy)-15,15-diethyl-11-(4-methoxybenzyloxy)-2,2,3,3,10,12-hexamethyl-4,14-dioxa-3,15-disilaheptadecane (929883-06-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -5 °C

2: lithium borohydride / diethyl ether; H₂O / 1 h / 0 °C

3: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h / 20 °C

4: 91 percent / BH₃*THF; Sc(OTf)3 / CH₂Cl₂; tetrahydrofuran / 1 h

5: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h

With 2,6-dimethylpyridine; lithium borohydride; borane-THF; pyridinium p-toluenesulfonate; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1002/anie.200603654

upstream raw materials:

(2S,3R,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyldecan-1-ol

triethylsilyl trifluoromethyl sulfonate

(R)-3-((2R,3S,4S,5R,7R,9S)-10-(benzyloxy)-7,9-bis(tert-butyldimethylsilyloxy)-3,5-dihydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one

(R)-3-((2R,3S,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one

Downstream raw materials:

(2S,4R,6R,7R,8R,9S)-2,4,6-tris(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-7,9-dimethyl-10-(triethylsilyloxy)decan-1-ol

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