(5S,11S,13aR)-5-Benzyl-11-[7-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-heptyl]-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone

Base Information

• Chemical Name: (5S,11S,13aR)-5-Benzyl-11-[7-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-heptyl]-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone
• CAS No.: 887277-70-5
• Molecular Formula: C₃₃H₅₄N₄O₆Si
• Molecular Weight: 630.9
• Mol file: 887277-70-5.mol

Synonyms:(5S,11S,13aR)-5-Benzyl-11-[7-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-heptyl]-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone

Chemical Property of (5S,11S,13aR)-5-Benzyl-11-[7-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-heptyl]-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,11S,13aR)-5-Benzyl-11-[7-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-heptyl]-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone

There total 10 articles about (5S,11S,13aR)-5-Benzyl-11-[7-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-heptyl]-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone 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: 91.0%

(5S,11S,13aR)-5-Benzyl-11-(6,7-dihydroxy-heptyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone (887277-69-2) + tert-butyldimethylsilyl chloride (18162-48-6) → (5S,11S,13aR)-5-Benzyl-11-[7-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-heptyl]-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone (887277-70-5)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 8h;

DOI:10.1016/j.bmc.2005.12.063

Reference yield:

Boc-L-Ae9-Aib-L-Phe-D-Pro-OtBu (887277-60-3) → (5S,11S,13aR)-5-Benzyl-11-[7-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-heptyl]-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone (887277-70-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / 3 h / 0 °C

2: 87 percent / [O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium]PF₆; DIEA / dimethylformamide / 3 h

3: 100 percent / 4-methylmorpholine-N-oxide; water / microencapsulated osmium tetroxide / acetone; acetonitrile / 18 h

4: 91 percent / diisopropylethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 8 h

With dmap; water; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; HATU; osmium(VIII) oxide; In dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/j.bmc.2005.12.063

Reference yield:

cyclo(-L-Ae9-Aib-L-Phe-D-Pro-) (887277-64-7) → (5S,11S,13aR)-5-Benzyl-11-[7-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-heptyl]-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone (887277-70-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 4-methylmorpholine-N-oxide; water / microencapsulated osmium tetroxide / acetone; acetonitrile / 18 h

2: 91 percent / diisopropylethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 8 h

With dmap; water; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; osmium(VIII) oxide; In dichloromethane; acetone; acetonitrile;

DOI:10.1016/j.bmc.2005.12.063

upstream raw materials:

(5S,11S,13aR)-5-Benzyl-11-(6,7-dihydroxy-heptyl)-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone

tert-butyldimethylsilyl chloride

cyclo(-L-Ae₉-Aib-L-Phe-D-Pro-)

Boc-L-Ae₉-Aib-L-Phe-D-Pro-OtBu

Downstream raw materials:

(5S,11S,13aR)-5-Benzyl-11-[7-(tert-butyl-dimethyl-silanyloxy)-6-oxo-heptyl]-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone