methyl (4E,2S,3R)-3-acetoxy-2-benzamido-2-dimethylphenylsilylmethyl-6-(t-butyldiphenylsilyloxy)-4-hexenoate

Base Information

Chemical Name:methyl (4E,2S,3R)-3-acetoxy-2-benzamido-2-dimethylphenylsilylmethyl-6-(t-butyldiphenylsilyloxy)-4-hexenoate
CAS No.:389807-15-2
Molecular Formula:C₄₁H₄₉NO₆Si₂
Molecular Weight:708.014
Hs Code.:

Synonyms:methyl (4E,2S,3R)-3-acetoxy-2-benzamido-2-dimethylphenylsilylmethyl-6-(t-butyldiphenylsilyloxy)-4-hexenoate

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Chemical Property of methyl (4E,2S,3R)-3-acetoxy-2-benzamido-2-dimethylphenylsilylmethyl-6-(t-butyldiphenylsilyloxy)-4-hexenoate

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Technology Process of methyl (4E,2S,3R)-3-acetoxy-2-benzamido-2-dimethylphenylsilylmethyl-6-(t-butyldiphenylsilyloxy)-4-hexenoate

There total 11 articles about methyl (4E,2S,3R)-3-acetoxy-2-benzamido-2-dimethylphenylsilylmethyl-6-(t-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: 96.0%

: 67-56-1
methanol

: 389807-11-8
(1'R,4S,2'E)-4-[1'-acetoxy-4'-(tert-butyldiphenylsilyloxy)but-2'-en-1'-yl]-4-(dimethylphenylsilyl)methyl-2-phenyl-4,5-dihydro-5-oxazolone

: 389807-15-2
methyl (4E,2S,3R)-3-acetoxy-2-benzamido-2-dimethylphenylsilylmethyl-6-(t-butyldiphenylsilyloxy)-4-hexenoate

Guidance literature:: With (+)-10-camphorsulfonic acid; In diethyl ether; at 25 ℃; for 72h;
DOI:10.1021/ja0118338

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 389807-15-2
methyl (4E,2S,3R)-3-acetoxy-2-benzamido-2-dimethylphenylsilylmethyl-6-(t-butyldiphenylsilyloxy)-4-hexenoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / imidazole

2.1: 67 percent / PCC; Cellite / CH₂Cl₂

3.1: 99 percent / FeCl₃ / CH₂Cl₂ / 0 °C / 0.5 Torr

4.1: NaH / tetrahydrofuran / 25 °C / Irradiation

4.2: (η³-C3H5PdCl)2; (R,R)-1,2-(o-PPh2-C6H4-CO-NH)2-cyclohexane / tetrahydrofuran / 25 °C

4.3: 68 percent / tetrahydrofuran / 3 h / 0 °C

5.1: 96 percent / (+)-camphorsulfonic acid / diethyl ether / 72 h / 25 °C

With 1H-imidazole; silica gel; iron(III) chloride; sodium hydride; (+)-10-camphorsulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja0118338

Reference yield:

: 101649-82-5
N-benzoyl-2-bromoglycine methyl ester

: 389807-15-2
methyl (4E,2S,3R)-3-acetoxy-2-benzamido-2-dimethylphenylsilylmethyl-6-(t-butyldiphenylsilyloxy)-4-hexenoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 61 percent / tetrahydrofuran / 3 h / -78 - 0 °C

2.1: 94 percent / LiOH / tetrahydrofuran; H₂O / 8 h / 25 °C

3.1: 97 percent / DCC / tetrahydrofuran / 12 h / 25 °C

4.1: NaH / tetrahydrofuran / 25 °C / Irradiation

4.2: (η³-C3H5PdCl)2; (R,R)-1,2-(o-PPh2-C6H4-CO-NH)2-cyclohexane / tetrahydrofuran / 25 °C

4.3: 68 percent / tetrahydrofuran / 3 h / 0 °C

5.1: 96 percent / (+)-camphorsulfonic acid / diethyl ether / 72 h / 25 °C

With lithium hydroxide; sodium hydride; (+)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; water;
DOI:10.1021/ja0118338