[(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]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(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]-carbamic acid benzyl ester
• CAS No.: 401606-68-6
• Molecular Formula: C₄₁H₅₇N₃O₈Si
• Molecular Weight: 748.004

Synonyms:[(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]-carbamic acid benzyl ester

Chemical Property of [(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]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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]-carbamic acid benzyl ester

There total 7 articles about [(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]-carbamic 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: 88.0%

[(3R,4R,7S,10S,11R)-15-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-7-isopropyl-4-methoxymethoxymethyl-3-methyl-6,9-dioxo-2-oxa-5,8-diaza-bicyclo[10.3.1]hexadeca-1(15),12(16),13-trien-10-yl]-carbamic acid benzyl ester (401606-67-5) → [(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]-carbamic acid benzyl ester (401606-68-6)

Guidance literature:

With bromocatecholborane; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/ja017277z

Reference yield:

t-Boc-L-valine (13734-41-3) → [(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]-carbamic acid benzyl ester (401606-68-6)

Guidance literature:

Multi-step reaction with 5 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

With 2,6-dimethylpyridine; lithium hydroxide; i-Pr₂NEt₂; bromocatecholborane; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; 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,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]-carbamic acid benzyl ester (401606-68-6)

Guidance literature:

Multi-step reaction with 5 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

With 2,6-dimethylpyridine; lithium hydroxide; i-Pr₂NEt₂; bromocatecholborane; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ja017277z

upstream raw materials:

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

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

(2S,3R)-3-{3-[(1R,2R)-2-((S)-2-Amino-3-methyl-butyrylamino)-1-ethyl-3-methoxymethoxy-1-methyl-propoxy]-4-benzyloxy-phenyl}-2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

Downstream raw materials:

(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

[((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

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

({(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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