2-{(R)-3-[(2R,3R,4R)-4-(Benzyloxycarbonyl-methyl-amino)-5-methoxy-2,3-bis-triethylsilanyloxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester

Base Information

Chemical Name:2-{(R)-3-[(2R,3R,4R)-4-(Benzyloxycarbonyl-methyl-amino)-5-methoxy-2,3-bis-triethylsilanyloxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester
CAS No.:139462-39-8
Molecular Formula:C₃₆H₆₁N₃O₉Si₂
Molecular Weight:736.066
Hs Code.:

2-{(R)-3-[(2R,3R,4R)-4-(Benzyloxycarbonyl-methyl-amino)-5-methoxy-2,3-bis-triethylsilanyloxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester

Synonyms:2-{(R)-3-[(2R,3R,4R)-4-(Benzyloxycarbonyl-methyl-amino)-5-methoxy-2,3-bis-triethylsilanyloxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 2-{(R)-3-[(2R,3R,4R)-4-(Benzyloxycarbonyl-methyl-amino)-5-methoxy-2,3-bis-triethylsilanyloxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 2-{(R)-3-[(2R,3R,4R)-4-(Benzyloxycarbonyl-methyl-amino)-5-methoxy-2,3-bis-triethylsilanyloxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester

There total 21 articles about 2-{(R)-3-[(2R,3R,4R)-4-(Benzyloxycarbonyl-methyl-amino)-5-methoxy-2,3-bis-triethylsilanyloxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester 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:

: 39608-31-6
N-(Benzyloxycarbonyl)sarcosine

: 139462-39-8
2-{(R)-3-[(2R,3R,4R)-4-(Benzyloxycarbonyl-methyl-amino)-5-methoxy-2,3-bis-triethylsilanyloxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: Et₃N / diethyl ether / 1 h / 0 °C

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, a) -78 deg C, 15 min, b) 0 deg C, 30 min

3: 1.) TiCl₄, diisopropylethylamine, 2.) BF₃*Et₂O / 1.) CH₂Cl₂, 0 deg C, 3 h, 2.) CH₂Cl₂, 25 deg C, 2 h

4: 93 percent / LiBH₄ / methanol; tetrahydrofuran / 0.67 h / 0 °C

5: 1.) oxalyl chloride, DMSO, 2.) diisopropylethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -50 deg C, 1 h

6: 1.) Sn(OTf)2, Et₃N, 2.) TMEDA

7: AlMe₃ / CH₂Cl₂; toluene / 4 h / 25 °C

8: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; lithium borohydride; tin(II) trifluoromethanesulfonate; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; trimethylaluminum; titanium tetrachloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja00050a024

Reference yield:

: 136546-79-7
<4S,3(2R)>-4-benzyl-3-<4-(tert-butoxycarbonyl)-2-methylbutanoyl>-2-oxazolidinone

: 139462-39-8
2-{(R)-3-[(2R,3R,4R)-4-(Benzyloxycarbonyl-methyl-amino)-5-methoxy-2,3-bis-triethylsilanyloxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 100 percent / TFA / CH₂Cl₂

2: 71 percent / Et₃N, diphenylphosphoryl azide / 15 h / Heating

3: 96 percent / 30percent aq. H₂O₂, LiOH / tetrahydrofuran; H₂O / 0.5 h / 0 °C

4: N-methylmorpholine / tetrahydrofuran / 0.25 h / -23 °C

5: tetrahydrofuran / Ambient temperature

6: 78 percent / pyridine, thionyl chloride / diethyl ether; tetrahydrofuran / 2 h / 0 °C

7: 88 percent / 4-(dimethylamine)pyridine / acetonitrile / 37 h / 25 °C

8: 1.) KHMDS / 1.) THF, -78 deg C, 10 min, 2.) THF, a) -78 deg C, 15 min, b) from -78 deg C to RT

9: pyridine, 30percent aq. H₂O₂ / CH₂Cl₂ / 1 h / 0 °C

10: HCl(g) / ethyl acetate / 0.33 h / 0 °C

11: AlMe₃ / CH₂Cl₂; toluene / 4 h / 25 °C

12: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; lithium hydroxide; thionyl chloride; diphenylphosphoranyl azide; dihydrogen peroxide; trimethylaluminum; potassium hexamethylsilazane; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; toluene; acetonitrile;
DOI:10.1021/ja00050a024

Reference yield:

: 139462-24-1
<2S>-2--N-methylamino>-3-methoxy-1-propanol

: 139462-39-8
2-{(R)-3-[(2R,3R,4R)-4-(Benzyloxycarbonyl-methyl-amino)-5-methoxy-2,3-bis-triethylsilanyloxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) oxalyl chloride, DMSO, 2.) diisopropylethylamine / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -50 deg C, 1 h

2: 1.) Sn(OTf)2, Et₃N, 2.) TMEDA

3: AlMe₃ / CH₂Cl₂; toluene / 4 h / 25 °C

4: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; trimethylaluminum; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;
DOI:10.1021/ja00050a024