(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-triisopropylsilanyloxymethyl-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester

Base Information

• Chemical Name: (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-triisopropylsilanyloxymethyl-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester
• CAS No.: 871483-74-8
• Molecular Formula: C₅₇H₇₇N₃O₁₀Si
• Molecular Weight: 992.338
• Mol file: 871483-74-8.mol

Synonyms:(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-triisopropylsilanyloxymethyl-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester

Chemical Property of (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-triisopropylsilanyloxymethyl-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-triisopropylsilanyloxymethyl-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester

There total 15 articles about (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-triisopropylsilanyloxymethyl-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl 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:

(2R,3S)-2-Hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-ol → (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-triisopropylsilanyloxymethyl-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester (871483-74-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 2,6-lutidine / -5 °C

2: 96 percent / (COCl)2; DMSO; Et₃N / -78 °C

3: 96 percent / I₂; pyridine / CH₂Cl₂

4: 67 percent / NaBH₄; CeCl₃*7H₂O / methanol

5: 57 percent / DIAD; PPh₃ / tetrahydrofuran / 20 °C

6: 72 percent / n-BuLi / tetrahydrofuran / -78 °C

7: 96 percent / NaBH₄; CeCl₃*7H₂O / methanol

8: 78 percent / (PPh₃)3RhCl; H₂

9: 92 percent / NaH / tetrahydrofuran

10: 90 percent / Na; naphthalene

11: 90 percent / K₂CO₃

12: aq. KOH / tetrahydrofuran / 0 °C

13: pyBOP; HOBt; DIPEA / CH₂Cl₂

With pyridine; 2,6-dimethylpyridine; potassium hydroxide; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; cerium(III) chloride; oxalyl dichloride; naphthalene; di-isopropyl azodicarboxylate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; iodine; sodium; sodium hydride; potassium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 2: Swern oxidation / 4: Luche reduction / 5: Mitsunobu reaction / 7: Luche reduction;

DOI:10.1016/j.bmcl.2005.08.062

Reference yield:

Acetic acid (2R,3S)-2-acetoxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl ester → (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-triisopropylsilanyloxymethyl-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester (871483-74-8)

Guidance literature:

Multi-step reaction with 14 steps

1: K₂CO₃; MeOH

2: 2,6-lutidine / -5 °C

3: 96 percent / (COCl)2; DMSO; Et₃N / -78 °C

4: 96 percent / I₂; pyridine / CH₂Cl₂

5: 67 percent / NaBH₄; CeCl₃*7H₂O / methanol

6: 57 percent / DIAD; PPh₃ / tetrahydrofuran / 20 °C

7: 72 percent / n-BuLi / tetrahydrofuran / -78 °C

8: 96 percent / NaBH₄; CeCl₃*7H₂O / methanol

9: 78 percent / (PPh₃)3RhCl; H₂

10: 92 percent / NaH / tetrahydrofuran

11: 90 percent / Na; naphthalene

12: 90 percent / K₂CO₃

13: aq. KOH / tetrahydrofuran / 0 °C

14: pyBOP; HOBt; DIPEA / CH₂Cl₂

With pyridine; 2,6-dimethylpyridine; methanol; potassium hydroxide; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; cerium(III) chloride; oxalyl dichloride; naphthalene; di-isopropyl azodicarboxylate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; iodine; sodium; sodium hydride; potassium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 3: Swern oxidation / 5: Luche reduction / 6: Mitsunobu reaction / 8: Luche reduction;

DOI:10.1016/j.bmcl.2005.08.062

Reference yield:

(2R,3S,6S)-6-Isobutoxy-2-triisopropylsilanyloxymethyl-3,6-dihydro-2H-pyran-3-ol (871483-61-3) → (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-triisopropylsilanyloxymethyl-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester (871483-74-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 96 percent / (COCl)2; DMSO; Et₃N / -78 °C

2: 96 percent / I₂; pyridine / CH₂Cl₂

3: 67 percent / NaBH₄; CeCl₃*7H₂O / methanol

4: 57 percent / DIAD; PPh₃ / tetrahydrofuran / 20 °C

5: 72 percent / n-BuLi / tetrahydrofuran / -78 °C

6: 96 percent / NaBH₄; CeCl₃*7H₂O / methanol

7: 78 percent / (PPh₃)3RhCl; H₂

8: 92 percent / NaH / tetrahydrofuran

9: 90 percent / Na; naphthalene

10: 90 percent / K₂CO₃

11: aq. KOH / tetrahydrofuran / 0 °C

12: pyBOP; HOBt; DIPEA / CH₂Cl₂

With pyridine; potassium hydroxide; sodium tetrahydroborate; Wilkinson's catalyst; n-butyllithium; cerium(III) chloride; oxalyl dichloride; naphthalene; di-isopropyl azodicarboxylate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; iodine; sodium; sodium hydride; potassium carbonate; benzotriazol-1-ol; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 1: Swern oxidation / 3: Luche reduction / 4: Mitsunobu reaction / 6: Luche reduction;

DOI:10.1016/j.bmcl.2005.08.062

upstream raw materials:

Asp(OBzl)-Phe-OBzl

(2R,3S,6S)-6-Isobutoxy-2-triisopropylsilanyloxymethyl-3,6-dihydro-2H-pyran-3-ol

(2R,6S)-6-Isobutoxy-2-triisopropylsilanyloxymethyl-6H-pyran-3-one

(2R,6S)-4-Iodo-6-isobutoxy-2-triisopropylsilanyloxymethyl-6H-pyran-3-one

Downstream raw materials:

(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[(3S,3aR,5S,7S,7aS)-3-benzyloxy-5-isobutoxy-7-(3-phenyl-propionyloxymethyl)-hexahydro-pyrano[3,4-b]pyrrol-1-yl]-acetylamino}-succinamic acid benzyl ester

(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-[2-((3S,3aR,5S,7S,7aS)-3-benzyloxy-7-hydroxymethyl-5-isobutoxy-hexahydro-pyrano[3,4-b]pyrrol-1-yl)-acetylamino]-succinamic acid benzyl ester

Refernces