(3R,5S)-6-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzylamino)-hexanoic acid

Base Information

• Chemical Name: (3R,5S)-6-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzylamino)-hexanoic acid
• CAS No.: 130075-02-4
• Molecular Formula: C₂₂H₃₇NO₆Si
• Molecular Weight: 439.624

Synonyms:(3R,5S)-6-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzylamino)-hexanoic acid

Chemical Property of (3R,5S)-6-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzylamino)-hexanoic acid

Chemical Property:

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Technology Process of (3R,5S)-6-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzylamino)-hexanoic acid

There total 4 articles about (3R,5S)-6-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzylamino)-hexanoic acid 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:

(3R,2'S) N-(p-Methoxybenzyl)-3-(3'-acetoxy-2'-tert-butyldimethylylsiloxypropyl)-isoxazolidin-5-one (124005-30-7) → (3R,5S)-6-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzylamino)-hexanoic acid (130075-02-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)98815-4

Reference yield:

(2S)-acetic acid 6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester (63952-83-0) → (3R,5S)-6-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzylamino)-hexanoic acid (130075-02-4)

Guidance literature:

Multi-step reaction with 3 steps

1: ethanol / 3 h / Ambient temperature

2: DMAP / dimethylformamide / 3 h / Ambient temperature

3: H₂ / 10percent Pd/C / methanol / 0.67 h / Ambient temperature

With dmap; hydrogen; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)88341-1

Reference yield:

N-(4-methoxybenzyl)hydroxylamine (51307-59-6) → (3R,5S)-6-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzylamino)-hexanoic acid (130075-02-4)

Guidance literature:

Multi-step reaction with 3 steps

1: ethanol / 3 h / Ambient temperature

2: DMAP / dimethylformamide / 3 h / Ambient temperature

3: H₂ / 10percent Pd/C / methanol / 0.67 h / Ambient temperature

With dmap; hydrogen; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)88341-1

upstream raw materials:

(3R,2'S) N-(p-Methoxybenzyl)-3-(3'-acetoxy-2'-tert-butyldimethylylsiloxypropyl)-isoxazolidin-5-one

(2S)-acetic acid 6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester

N-(4-methoxybenzyl)hydroxylamine

Acetic acid (S)-2-hydroxy-3-[(R)-2-(4-methoxy-benzyl)-5-oxo-isoxazolidin-3-yl]-propyl ester

Downstream raw materials:

Acetic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(R)-1-(4-methoxy-benzyl)-4-oxo-azetidin-2-yl]-propyl ester

[(R)-1-(4-Methoxy-benzyl)-4-oxo-azetidin-2-yl]-acetaldehyde

(R)-4-((S)-2,3-Dihydroxy-propyl)-1-(4-methoxy-benzyl)-azetidin-2-one

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