Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate

Base Information

• Chemical Name: Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate
• CAS No.: 145655-06-7
• Molecular Formula: C₃₁H₄₇NO₅Si
• Molecular Weight: 541.803

Synonyms:Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate

Chemical Property of Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate

Chemical Property:

Purity/Quality:

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Technology Process of Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate

There total 13 articles about Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate 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: 89.0%

Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenyl-2(E)-hexenoate (145655-11-4) → Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate (145655-06-7)

Guidance literature:

With sodium tetrahydroborate; nickel dichloride; In methanol; a) 0 deg C, 1 h, b) r.t., 18 h;

DOI:10.1016/S0040-4039(00)60888-2

Reference yield:

(1'R,2'S)-2-<2-(N-benzyl-N-tert-butoxycarbonylamino)-1-hydroxy-3-phenylpropyl>-1,3-thiazole (145655-01-2) → Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate (145655-06-7)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N, DMAP / dimethylformamide / 1 h / Ambient temperature

2: molecular sieves 4 Angstroem / acetonitrile / 0.25 h / Ambient temperature

3: 1.) NaBH₄, 2.) aq. HgCl₂ / 1.) MeOH, r.t., 10 min, 2.) CH₃CN, r.t., 15 min

4: toluene / 24 h / Ambient temperature

5: NiCl₂*6H₂O, NaBH₄ / methanol / 1.) 0 deg C, 1 h, 2.) r.t., 18 h

With dmap; sodium tetrahydroborate; 4 A molecular sieve; triethylamine; mercury dichloride; nickel dichloride; In methanol; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo00129a037

Reference yield:

(2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal (145655-02-3) → Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate (145655-06-7)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 24 h / Ambient temperature

2: NiCl₂*6H₂O, NaBH₄ / methanol / 1.) 0 deg C, 1 h, 2.) r.t., 18 h

With sodium tetrahydroborate; nickel dichloride; In methanol; toluene;

DOI:10.1021/jo00129a037

upstream raw materials:

Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenyl-2(E)-hexenoate

t-butyldimethylsiyl triflate

(1'R,2'S)-2-<2-(N-benzyl-N-tert-butoxycarbonylamino)-1-hydroxy-3-phenylpropyl>-1,3-thiazole

(2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

Downstream raw materials:

(5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one

(5S,1'S)-5-<1'--3'-methylbutyl>dihydrofuran-2(3H)-one

(3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one

(3R,5S,1'S)-3-Benzyl-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one

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