Heptanoic acid, 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-3-oxo-6-[[(phenylmeth oxy)carbonyl]amino]-, methyl ester, (5S,6S)-

Base Information

Chemical Name:Heptanoic acid, 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-3-oxo-6-[[(phenylmeth oxy)carbonyl]amino]-, methyl ester, (5S,6S)-
CAS No.:823235-74-1
Molecular Formula:C22H35NO7Si
Molecular Weight:453.608
Hs Code.:

Synonyms:(6S)-6-benzyloxycarbonylamino-7-(tert-butyldimethylsilanyloxy)-(5S)-5-hydroxy-3-oxoheptanoic acid methyl ester;(5S,6S)-6-Benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-heptanoic acid methyl ester;

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Chemical Property of Heptanoic acid, 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-3-oxo-6-[[(phenylmeth oxy)carbonyl]amino]-, methyl ester, (5S,6S)-

Chemical Property:

PSA：111.16000
LogP:3.57730

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of Heptanoic acid, 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-3-oxo-6-[[(phenylmeth oxy)carbonyl]amino]-, methyl ester, (5S,6S)-

There total 4 articles about Heptanoic acid, 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-3-oxo-6-[[(phenylmeth oxy)carbonyl]amino]-, methyl ester, (5S,6S)- 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: 85.0%

: 67-56-1
methanol

: 359455-05-3
[(1S,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-2-hydroxy-propyl]-carbamic acid benzyl ester

: 823235-74-1
(5S,6S)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-heptanoic acid methyl ester

Guidance literature:: In toluene; for 4h; Heating;
DOI:10.1021/ol048068x DOI:10.1021/jo701402b

Reference yield:

: 154161-05-4
L-N-(benzyloxycarbonyl)-O-<(1,1-dimethylethyl)dimethylsilyloxy>serine methyl ester

: 823235-74-1
(5S,6S)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: methanol; lithium borohydride / tetrahydrofuran; diethyl ether / 3 h / Reflux

2: dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane / 1 h / 0 °C

3: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / dichloromethane / 24 h / 0 - 20 °C

4: toluene / 4 h / Reflux

With methanol; lithium borohydride; tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 2: |Parikh-Doering Oxidation / 3: |Aldol Addition;
DOI:10.1021/jacs.1c09616

Reference yield:

: 154659-09-3
(R)-benzyl (1-((tert-butyldimethylsilyl)oxy)-3-hydroxypropan-2-yl)carbamate

: 823235-74-1
(5S,6S)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane / 1 h / 0 °C

2: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / dichloromethane / 24 h / 0 - 20 °C

3: toluene / 4 h / Reflux

With tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; 1: |Parikh-Doering Oxidation / 2: |Aldol Addition;
DOI:10.1021/jacs.1c09616