(2S,6R)-2-[(R)-4-((S)-2-Benzyloxycarbonylamino-propionylamino)-4-methoxycarbonyl-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid 7-methyl ester 1-(2-trimethylsilanyl-ethyl) ester

Base Information

• Chemical Name: (2S,6R)-2-[(R)-4-((S)-2-Benzyloxycarbonylamino-propionylamino)-4-methoxycarbonyl-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid 7-methyl ester 1-(2-trimethylsilanyl-ethyl) ester
• CAS No.: 478920-24-0
• Molecular Formula: C₃₅H₅₆N₄O₁₂Si
• Molecular Weight: 752.935

Synonyms:

Chemical Property of (2S,6R)-2-[(R)-4-((S)-2-Benzyloxycarbonylamino-propionylamino)-4-methoxycarbonyl-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid 7-methyl ester 1-(2-trimethylsilanyl-ethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6R)-2-[(R)-4-((S)-2-Benzyloxycarbonylamino-propionylamino)-4-methoxycarbonyl-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid 7-methyl ester 1-(2-trimethylsilanyl-ethyl) ester

There total 14 articles about (2S,6R)-2-[(R)-4-((S)-2-Benzyloxycarbonylamino-propionylamino)-4-methoxycarbonyl-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid 7-methyl ester 1-(2-trimethylsilanyl-ethyl) 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:

2-(Trimethylsilyl)ethanol (2916-68-9) → (2S,6R)-2-[(R)-4-((S)-2-Benzyloxycarbonylamino-propionylamino)-4-methoxycarbonyl-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid 7-methyl ester 1-(2-trimethylsilanyl-ethyl) ester (478920-24-0)

Guidance literature:

Multi-step reaction with 5 steps

1: LiHMDS / tetrahydrofuran / 0 °C

2: H₂ / 10percent Pd/C / methanol

3: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

4: H₂ / 10percent Pd/C / methanol

5: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; lithium hexamethyldisilazane; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8

Reference yield:

(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde (89969-26-6) → (2S,6R)-2-[(R)-4-((S)-2-Benzyloxycarbonylamino-propionylamino)-4-methoxycarbonyl-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid 7-methyl ester 1-(2-trimethylsilanyl-ethyl) ester (478920-24-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: KHMDS / tetrahydrofuran / 0.25 h / -78 - -55 °C

1.2: 76 percent / tetrahydrofuran / -78 - -30 °C

2.1: 65 percent / LiHMDS / tetrahydrofuran / 0 °C

3.1: H₂ / Pd(OH)2/C / methanol

4.1: NaHCO₃ / tetrahydrofuran; H₂O / 1 h

5.1: H₂ / 10percent Pd/C / methanol

6.1: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

7.1: H₂ / 10percent Pd/C / methanol

8.1: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; 1.2: Wittig-Horner reaction;

DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8

Reference yield:

(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester (58456-26-1) → (2S,6R)-2-[(R)-4-((S)-2-Benzyloxycarbonylamino-propionylamino)-4-methoxycarbonyl-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid 7-methyl ester 1-(2-trimethylsilanyl-ethyl) ester (478920-24-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 73 percent / LiAl(OtBu)3H / tetrahydrofuran / -78 °C

2.1: KHMDS / tetrahydrofuran / 0.25 h / -78 - -55 °C

2.2: 76 percent / tetrahydrofuran / -78 - -30 °C

3.1: 65 percent / LiHMDS / tetrahydrofuran / 0 °C

4.1: H₂ / Pd(OH)2/C / methanol

5.1: NaHCO₃ / tetrahydrofuran; H₂O / 1 h

6.1: H₂ / 10percent Pd/C / methanol

7.1: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

8.1: H₂ / 10percent Pd/C / methanol

9.1: PyBOP; NMM / CH₂Cl₂ / 20 °C / pH 9 - 9.5

With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; potassium hexamethylsilazane; sodium hydrogencarbonate; lithium tri-t-butoxyaluminum hydride; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; 2.2: Wittig-Horner reaction;

DOI:10.1002/1099-0690(200208)2002:16<2710::AID-EJOC2710>3.0.CO;2-8

upstream raw materials:

N-Cbz-Ala

2-(Trimethylsilyl)ethanol

(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde

(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester

Downstream raw materials:

1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-3-O-{(2R)-propionyl-[L-alanyl-(D-isoglutamyl α-methyl ester)-(7-methyl)-1-(2-trimethylsilylethyl) (2S,6R)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate]-2-yl}-β-D-glucopyranose

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