{[(3R,4S,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-7-isopropyl-3-methyl-10-(2-nitro-benzenesulfonylamino)-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-4-carbonyl]-amino}-acetic acid benzyl ester

Base Information

• Chemical Name: {[(3R,4S,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-7-isopropyl-3-methyl-10-(2-nitro-benzenesulfonylamino)-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-4-carbonyl]-amino}-acetic acid benzyl ester
• CAS No.: 401606-71-1
• Molecular Formula: C₄₈H₆₁N₅O₁₂SSi
• Molecular Weight: 960.19

Synonyms:{[(3R,4S,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-7-isopropyl-3-methyl-10-(2-nitro-benzenesulfonylamino)-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-4-carbonyl]-amino}-acetic acid benzyl ester

Chemical Property of {[(3R,4S,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-7-isopropyl-3-methyl-10-(2-nitro-benzenesulfonylamino)-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-4-carbonyl]-amino}-acetic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {[(3R,4S,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-7-isopropyl-3-methyl-10-(2-nitro-benzenesulfonylamino)-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-4-carbonyl]-amino}-acetic acid benzyl ester

There total 13 articles about {[(3R,4S,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-7-isopropyl-3-methyl-10-(2-nitro-benzenesulfonylamino)-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-4-carbonyl]-amino}-acetic 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:

t-Boc-L-valine (13734-41-3) → {[(3R,4S,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-7-isopropyl-3-methyl-10-(2-nitro-benzenesulfonylamino)-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1(15),12(16),13-triene-4-carbonyl]-amino}-acetic acid benzyl ester (401606-71-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 454 mg / DEBPT; i-Pr₂NEt₂ / tetrahydrofuran / 18 h / 20 °C

2: 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

3: 143 mg / aq. LiOH / 2-methyl-propan-2-ol / 16 h / 20 °C

4: 78 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole / dimethylformamide; CH₂Cl₂ / 24 h / 0 - 20 °C

5: 88 percent / β-bromocatecholborane / CH2Cl2 / 0.5 h / -78 °C

6: H₂; 2,2'-bipyridyl / Pd/C / methanol; ethyl acetate / 2 h

7: 37.7 mg / 2,4,6-collidine / CH₂Cl₂ / 3 h / 20 °C

8: Dess-Martin periodinane / CH₂Cl₂ / 1.25 h / 0 - 25 °C

9: aq. NaClO₂; NaH₂PO₄*2H₂O / 2-methyl-propan-2-ol; various solvent(s) / 0.33 h / 25 °C

10: 28.4 mg / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; i-Pr₂NEt₂ / tetrahydrofuran / 18 h / 20 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; [2,2]bipyridinyl; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; i-Pr₂NEt₂; bromocatecholborane; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ja017277z

Reference yield:

(2S,3R)-3-[3-((1R,2R)-2-Amino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-4-benzyloxy-phenyl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl ester → {[(3R,4S,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-7-isopropyl-3-methyl-10-(2-nitro-benzenesulfonylamino)-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1(15),12(16),13-triene-4-carbonyl]-amino}-acetic acid benzyl ester (401606-71-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 454 mg / DEBPT; i-Pr₂NEt₂ / tetrahydrofuran / 18 h / 20 °C

2: 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

3: 143 mg / aq. LiOH / 2-methyl-propan-2-ol / 16 h / 20 °C

4: 78 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole / dimethylformamide; CH₂Cl₂ / 24 h / 0 - 20 °C

5: 88 percent / β-bromocatecholborane / CH2Cl2 / 0.5 h / -78 °C

6: H₂; 2,2'-bipyridyl / Pd/C / methanol; ethyl acetate / 2 h

7: 37.7 mg / 2,4,6-collidine / CH₂Cl₂ / 3 h / 20 °C

8: Dess-Martin periodinane / CH₂Cl₂ / 1.25 h / 0 - 25 °C

9: aq. NaClO₂; NaH₂PO₄*2H₂O / 2-methyl-propan-2-ol; various solvent(s) / 0.33 h / 25 °C

10: 28.4 mg / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; i-Pr₂NEt₂ / tetrahydrofuran / 18 h / 20 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; [2,2]bipyridinyl; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; i-Pr₂NEt₂; bromocatecholborane; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ja017277z

Reference yield:

(2S,3R)-3-[4-Benzyloxy-3-((1R,2R)-2-tert-butoxycarbonylamino-1-ethyl-3-methoxymethoxy-1-methyl-propoxy)-phenyl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl ester (401606-63-1) → {[(3R,4S,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-7-isopropyl-3-methyl-10-(2-nitro-benzenesulfonylamino)-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1(15),12(16),13-triene-4-carbonyl]-amino}-acetic acid benzyl ester (401606-71-1)

Guidance literature:

Multi-step reaction with 11 steps

1: TFA / CH₂Cl₂ / 0.58 h / 0 °C

2: 454 mg / DEBPT; i-Pr₂NEt₂ / tetrahydrofuran / 18 h / 20 °C

3: 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

4: 143 mg / aq. LiOH / 2-methyl-propan-2-ol / 16 h / 20 °C

5: 78 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl; 1-hydroxybenzotriazole / dimethylformamide; CH₂Cl₂ / 24 h / 0 - 20 °C

6: 88 percent / β-bromocatecholborane / CH2Cl2 / 0.5 h / -78 °C

7: H₂; 2,2'-bipyridyl / Pd/C / methanol; ethyl acetate / 2 h

8: 37.7 mg / 2,4,6-collidine / CH₂Cl₂ / 3 h / 20 °C

9: Dess-Martin periodinane / CH₂Cl₂ / 1.25 h / 0 - 25 °C

10: aq. NaClO₂; NaH₂PO₄*2H₂O / 2-methyl-propan-2-ol; various solvent(s) / 0.33 h / 25 °C

11: 28.4 mg / 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; i-Pr₂NEt₂ / tetrahydrofuran / 18 h / 20 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; [2,2]bipyridinyl; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; i-Pr₂NEt₂; bromocatecholborane; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ja017277z

upstream raw materials:

Gly-OBz

benzyl 2-aminoacetate hydrochloride

t-Boc-L-valine

(3R,4R,7S,10S,11R)-10-Amino-15-benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-4-hydroxymethyl-7-isopropyl-3-methyl-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-6,9-dione

Downstream raw materials:

({15-benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-7-isopropyl-3-methyl-10-[methyl-(2-nitro-benzenesulfonyl)-amino]-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-4-carbonyl}-amino)-acetic acid benzyl ester

[((3R,4S,7S,10S,11R)-15-Benzyloxy-3-ethyl-11-hydroxy-7-isopropyl-3-methyl-10-methylamino-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-4-carbonyl)-amino]-acetic acid benzyl ester

({(3R,4S,7S,10S,11R)-15-Benzyloxy-3-ethyl-11-hydroxy-7-isopropyl-3-methyl-10-[methyl-(2-nitro-benzenesulfonyl)-amino]-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-4-carbonyl}-amino)-acetic acid benzyl ester

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