N-[(3R,4R,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-4-hydroxymethyl-7-isopropyl-3-methyl-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-10-yl]-2-nitro-benzenesulfonamide

Base Information

• Chemical Name: N-[(3R,4R,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-4-hydroxymethyl-7-isopropyl-3-methyl-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-10-yl]-2-nitro-benzenesulfonamide
• CAS No.: 401606-70-0
• Molecular Formula: C₃₉H₅₄N₄O₁₀SSi
• Molecular Weight: 799.03

Synonyms:N-[(3R,4R,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-4-hydroxymethyl-7-isopropyl-3-methyl-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-10-yl]-2-nitro-benzenesulfonamide

Chemical Property of N-[(3R,4R,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-4-hydroxymethyl-7-isopropyl-3-methyl-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-10-yl]-2-nitro-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(3R,4R,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-4-hydroxymethyl-7-isopropyl-3-methyl-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-10-yl]-2-nitro-benzenesulfonamide

There total 9 articles about N-[(3R,4R,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-4-hydroxymethyl-7-isopropyl-3-methyl-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-10-yl]-2-nitro-benzenesulfonamide 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-Nitrobenzenesulfonyl chloride (1694-92-4) + (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 (401606-69-7) → N-[(3R,4R,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-4-hydroxymethyl-7-isopropyl-3-methyl-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1(15),12(16),13-trien-10-yl]-2-nitro-benzenesulfonamide (401606-70-0)

Guidance literature:

With 2,4,6-trimethyl-pyridine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/ja017277z

Reference yield:

t-Boc-L-valine (13734-41-3) → N-[(3R,4R,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-4-hydroxymethyl-7-isopropyl-3-methyl-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1(15),12(16),13-trien-10-yl]-2-nitro-benzenesulfonamide (401606-70-0)

Guidance literature:

Multi-step reaction with 7 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

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; [2,2]bipyridinyl; lithium hydroxide; i-Pr₂NEt₂; bromocatecholborane; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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 → N-[(3R,4R,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-4-hydroxymethyl-7-isopropyl-3-methyl-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1(15),12(16),13-trien-10-yl]-2-nitro-benzenesulfonamide (401606-70-0)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1021/ja017277z

upstream raw materials:

2-Nitrobenzenesulfonyl chloride

(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

t-Boc-L-valine

(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

Downstream raw materials:

[((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

({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-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

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