methyl (2S,3R,4E)-2-benzamido-2-methyl-3-hydroxy-6-(tert-butyldiphenylsilyloxy)-4-hexenoate

Base Information

• Chemical Name: methyl (2S,3R,4E)-2-benzamido-2-methyl-3-hydroxy-6-(tert-butyldiphenylsilyloxy)-4-hexenoate
• CAS No.: 389806-78-4
• Molecular Formula: C₃₁H₃₇NO₅Si
• Molecular Weight: 531.724

Synonyms:methyl (2S,3R,4E)-2-benzamido-2-methyl-3-hydroxy-6-(tert-butyldiphenylsilyloxy)-4-hexenoate

Chemical Property of methyl (2S,3R,4E)-2-benzamido-2-methyl-3-hydroxy-6-(tert-butyldiphenylsilyloxy)-4-hexenoate

Chemical Property:

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Technology Process of methyl (2S,3R,4E)-2-benzamido-2-methyl-3-hydroxy-6-(tert-butyldiphenylsilyloxy)-4-hexenoate

There total 2 articles about methyl (2S,3R,4E)-2-benzamido-2-methyl-3-hydroxy-6-(tert-butyldiphenylsilyloxy)-4-hexenoate 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:

methyl (2S,3R,4E)-3-acetoxy-2-benzamido-2-methyl-6-(tertbutyldiphenylsilyloxy)-4-hexenoate (211691-13-3) → methyl (2S,3R,4E)-2-benzamido-2-methyl-3-hydroxy-6-(tert-butyldiphenylsilyloxy)-4-hexenoate (389806-78-4)

Guidance literature:

With potassium carbonate;

DOI:10.1021/ja981141s

Reference yield:

(1'R,4S,2'E)-4-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)but-2'-en-1'-yl]-4-methyl-2-phenyl-4,5-dihydro-5-oxazolone (211691-11-1) → methyl (2S,3R,4E)-2-benzamido-2-methyl-3-hydroxy-6-(tert-butyldiphenylsilyloxy)-4-hexenoate (389806-78-4)

Guidance literature:

Multi-step reaction with 2 steps

1: TsOH*H₂O / 8 h / 25 °C

2: 2.05 g / K₂CO₃ / methanol / 0.5 h / 0 °C

With potassium carbonate; toluene-4-sulfonic acid; In methanol;

DOI:10.1021/ja0118338

Reference yield: 99.0%

methyl (2S,3R,4E)-2-benzamido-2-methyl-3-hydroxy-6-(tert-butyldiphenylsilyloxy)-4-hexenoate (389806-78-4) → (+)-(1'E,4S,5S)-5-[3'-t-butyldiphenylsilyloxy-prop-1'-enyl]-4-methyl-4-methoxycarbonyl-2-phenyl-4,5-dihydro-oxazole (211691-17-7)

Guidance literature:

With pyridine; methanesulfonyl chloride; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/ja0118338

upstream raw materials:

methyl (2S,3R,4E)-3-acetoxy-2-benzamido-2-methyl-6-(tertbutyldiphenylsilyloxy)-4-hexenoate

(1'R,4S,2'E)-4-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)but-2'-en-1'-yl]-4-methyl-2-phenyl-4,5-dihydro-5-oxazolone

Downstream raw materials:

(+)-(1'E,4S,5S)-5-[3'-t-butyldiphenylsilyloxy-prop-1'-enyl]-4-methyl-4-methoxycarbonyl-2-phenyl-4,5-dihydro-oxazole

(1'S,6S,3aS,6aR)-6-(2'-t-butyldophenylsilyloxy-1'-hydroxyethyl)-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

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