(2S,6R,7R)-(3E)-6-bromo-7-t-butyldimethylsilyloxy-1-p-methoxyphenylmethoxynon-3-ene-2,9-diol 9-pivaloate

Base Information

• Chemical Name: (2S,6R,7R)-(3E)-6-bromo-7-t-butyldimethylsilyloxy-1-p-methoxyphenylmethoxynon-3-ene-2,9-diol 9-pivaloate
• CAS No.: 143660-64-4
• Molecular Formula: C₂₈H₄₇BrO₆Si
• Molecular Weight: 587.667
• Mol file: 143660-64-4.mol

Synonyms:(2S,6R,7R)-(3E)-6-bromo-7-t-butyldimethylsilyloxy-1-p-methoxyphenylmethoxynon-3-ene-2,9-diol 9-pivaloate

Chemical Property of (2S,6R,7R)-(3E)-6-bromo-7-t-butyldimethylsilyloxy-1-p-methoxyphenylmethoxynon-3-ene-2,9-diol 9-pivaloate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6R,7R)-(3E)-6-bromo-7-t-butyldimethylsilyloxy-1-p-methoxyphenylmethoxynon-3-ene-2,9-diol 9-pivaloate

There total 8 articles about (2S,6R,7R)-(3E)-6-bromo-7-t-butyldimethylsilyloxy-1-p-methoxyphenylmethoxynon-3-ene-2,9-diol 9-pivaloate 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:

(2S,6R,7R)-(3E)-2-benzoyloxy-6-bromo-7-t-butyldimethylsilyloxy-1-p-methoxyphenylmethoxynon-3-en-9-ol 9-pivaloate (174874-22-7) → (2S,6R,7R)-(3E)-6-bromo-7-t-butyldimethylsilyloxy-1-p-methoxyphenylmethoxynon-3-ene-2,9-diol 9-pivaloate (143660-64-4)

Guidance literature:

With potassium carbonate; In methanol; water; at 25 ℃; for 3h; Yield given;

DOI:10.3987/com-95-s84

Reference yield:

(2S,6S,7R)-(3E)-6,7-epoxy-1-p-methoxyphenylmethoxynon-3-ene-2,9-diol 2-benzoate (143660-62-2) → (2S,6R,7R)-(3E)-6-bromo-7-t-butyldimethylsilyloxy-1-p-methoxyphenylmethoxynon-3-ene-2,9-diol 9-pivaloate (143660-64-4)

Guidance literature:

Multi-step reaction with 4 steps

1: Ti(O-i-Pr)4, Et₂NH*HBr / CH₂Cl₂ / 12 h / 25 °C

2: pyridine / CH₂Cl₂ / 12 h / 0 °C

3: TEA, DMAP / CH₂Cl₂ / 4 h / -20 °C

4: K₂CO₃ / methanol; H₂O / 3 h / 25 °C

With pyridine; titanium(IV) isopropylate; dmap; TEA; diethylamine hydrobromide; potassium carbonate; In methanol; dichloromethane; water;

DOI:10.3987/com-95-s84

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2S,6R,7R)-(3E)-6-bromo-7-t-butyldimethylsilyloxy-1-p-methoxyphenylmethoxynon-3-ene-2,9-diol 9-pivaloate (143660-64-4)

Guidance literature:

Multi-step reaction with 2 steps

1: TEA, DMAP / CH₂Cl₂ / 4 h / -20 °C

2: K₂CO₃ / methanol; H₂O / 3 h / 25 °C

With dmap; TEA; potassium carbonate; In methanol; dichloromethane; water;

DOI:10.3987/com-95-s84

upstream raw materials:

(2S,6R,7R)-(3E)-2-benzoyloxy-6-bromo-7-t-butyldimethylsilyloxy-1-p-methoxyphenylmethoxynon-3-en-9-ol 9-pivaloate

t-butyldimethylsiyl triflate

pivaloyl chloride

(2S,6S,7R)-(3E)-6,7-epoxy-1-p-methoxyphenylmethoxynon-3-ene-2,9-diol 2-benzoate

Downstream raw materials:

2,2-Dimethyl-propionic acid (3R,4R)-4-bromo-3-(tert-butyl-dimethyl-silanyloxy)-5-{(2R,3S)-3-[(R)-1-methanesulfonyloxy-2-(4-methoxy-benzyloxy)-ethyl]-oxiranyl}-pentyl ester

2,2-Dimethyl-propionic acid (3R,4R)-4-bromo-3-(tert-butyl-dimethyl-silanyloxy)-5-{(2R,3R)-3-[(R)-1-hydroxy-2-(4-methoxy-benzyloxy)-ethyl]-oxiranyl}-pentyl ester