(S)-2-[(2S,3R,4S)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(2S,3R,4S)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester
• CAS No.: 620960-74-9
• Molecular Formula: C₄₁H₆₂Br₂I₂N₆O₁₀Si₂
• Molecular Weight: 1268.77

Synonyms:(S)-2-[(2S,3R,4S)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

Chemical Property of (S)-2-[(2S,3R,4S)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (S)-2-[(2S,3R,4S)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

There total 18 articles about (S)-2-[(2S,3R,4S)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic 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: 60.0%

t-butyldimethylsiyl triflate (69739-34-0) + (S)-2-{(2S,3R,4S)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-dihydroxy-pentanoylamino}-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (620960-73-8) → (S)-2-[(2S,3R,4S)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (620960-74-9)

Guidance literature:

With 2,6-dimethylpyridine; potassium carbonate; In methanol; dichloromethane;

DOI:10.1016/j.tetlet.2003.08.105

Reference yield:

2,3,5-tri-O-benzyl-1-O-tertiobutyldimethylsilyl-D-ribitol (112929-28-9) → (S)-2-[(2S,3R,4S)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (620960-74-9)

Guidance literature:

Multi-step reaction with 20 steps

1: 90 percent / iPrO₂C-N=N-CO₂iPr; Ph₃P / tetrahydrofuran

2: 80 percent / NaOMe / methanol

3: 88 percent / DEAD; DPPA; Ph₃P / tetrahydrofuran

4: Ph₃P; H₂O / tetrahydrofuran

5: 92 percent / NaHCO₃ / dioxane; H₂O

6: H₂; CaCO₃ / Pd(OH)2/C / ethanol

7: pyridine

8: 89 percent / 2,6-lutidine / CH₂Cl₂

9: 92 percent / DIBAL-H / CH₂Cl₂

10: 93 percent / NaH / tetrahydrofuran

11: 86 percent / DMAP; Et₃N / tetrahydrofuran

12: 75 percent / CSA / methanol

13: NaN₃ / dimethylformamide

14: 85 percent / Cs₂CO₃ / methanol

15: TEMPO; NaClO₄; KBr / aq. NaHCO₃; acetone

16: BOP; Et₃N / dimethylformamide

17: 100 percent / TBAF

18: TFA / CH₂Cl₂

19: BOP; Et₃N / dimethylformamide

20: 60 percent / 2,6-lutidine; K₂CO₃ / methanol; CH₂Cl₂

With pyridine; 2,6-dimethylpyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium azide; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; diphenyl-phosphinic acid; sodium perchlorate; tetrabutyl ammonium fluoride; water; hydrogen; sodium methylate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; calcium carbonate; potassium bromide; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; sodium hydrogencarbonate; N,N-dimethyl-formamide; acetone; 1: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2003.08.105

Reference yield:

(2S,3R,4S)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-ol (620960-68-1) → (S)-2-[(2S,3R,4S)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (620960-74-9)

Guidance literature:

Multi-step reaction with 18 steps

1: 88 percent / DEAD; DPPA; Ph₃P / tetrahydrofuran

2: Ph₃P; H₂O / tetrahydrofuran

3: 92 percent / NaHCO₃ / dioxane; H₂O

4: H₂; CaCO₃ / Pd(OH)2/C / ethanol

5: pyridine

6: 89 percent / 2,6-lutidine / CH₂Cl₂

7: 92 percent / DIBAL-H / CH₂Cl₂

8: 93 percent / NaH / tetrahydrofuran

9: 86 percent / DMAP; Et₃N / tetrahydrofuran

10: 75 percent / CSA / methanol

11: NaN₃ / dimethylformamide

12: 85 percent / Cs₂CO₃ / methanol

13: TEMPO; NaClO₄; KBr / aq. NaHCO₃; acetone

14: BOP; Et₃N / dimethylformamide

15: 100 percent / TBAF

16: TFA / CH₂Cl₂

17: BOP; Et₃N / dimethylformamide

18: 60 percent / 2,6-lutidine; K₂CO₃ / methanol; CH₂Cl₂

With pyridine; 2,6-dimethylpyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium azide; camphor-10-sulfonic acid; diphenyl-phosphinic acid; sodium perchlorate; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; calcium carbonate; potassium bromide; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; sodium hydrogencarbonate; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tetlet.2003.08.105

upstream raw materials:

t-butyldimethylsiyl triflate

(S)-2-{(2S,3R,4S)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-dihydroxy-pentanoylamino}-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

2,3,5-tri-O-benzyl-1-O-tertiobutyldimethylsilyl-D-ribitol

(2S,3R,4S)-1,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-pentan-2-ol

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