(1S,2R,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-12-oxo-13-aza-19-oxapentacyclo<9.7.0^2,10.0^3,8.0^11,15>nonadec-16-ene 6,7-acetonide

Base Information

• Chemical Name: (1S,2R,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-12-oxo-13-aza-19-oxapentacyclo<9.7.0^2,10.0^3,8.0^11,15>nonadec-16-ene 6,7-acetonide
• CAS No.: 82770-11-4
• Molecular Formula: C₄₃H₅₉NO₆Si
• Molecular Weight: 714.03
• Mol file: 82770-11-4.mol

Synonyms:(1S,2R,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-12-oxo-13-aza-19-oxapentacyclo<9.7.0^2,10.0^3,8.0^11,15>nonadec-16-ene 6,7-acetonide

Chemical Property of (1S,2R,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-12-oxo-13-aza-19-oxapentacyclo<9.7.0^2,10.0^3,8.0^11,15>nonadec-16-ene 6,7-acetonide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-12-oxo-13-aza-19-oxapentacyclo<9.7.0^2,10.0^3,8.0^11,15>nonadec-16-ene 6,7-acetonide

There total 15 articles about (1S,2R,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-12-oxo-13-aza-19-oxapentacyclo<9.7.0^2,10.0^3,8.0^11,15>nonadec-16-ene 6,7-acetonide 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: 96.0%

(1S,2R,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-10-(benzoyloxy)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7-dihydroxy-5,7,16,17-tetramethyl-12-oxo-13-aza-19-oxapentacyclo<9.7.02,10.03,8.011,15>nonadec-16-ene 6,7-acetonide (82770-09-0) → (1S,2R,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-12-oxo-13-aza-19-oxapentacyclo<9.7.02,10.03,8.011,15>nonadec-16-ene 6,7-acetonide (82770-11-4)

Guidance literature:

With potassium tert-butylate; In diethyl ether; water; at 25 ℃; for 20h;

DOI:10.1021/ja00385a030

Reference yield: 93.0%

(1S,2R,3S,5R,6R,7S,8R,11R,14R,15S,18R)-2-(benzoyloxy)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7-dihydroxy-5,7,16,17-tetramethyl-10,12-dioxo-13-azatetracyclo<9.7.0.03,8.011,15>octadec-16-ene 6,7-acetonide (82770-10-3) → (1S,2R,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-12-oxo-13-aza-19-oxapentacyclo<9.7.02,10.03,8.011,15>nonadec-16-ene 6,7-acetonide (82770-11-4)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; at 25 ℃; for 4h;

DOI:10.1021/ja00385a030

Reference yield:

((S)-1-Phenyl-ethyl)-carbamic acid 2,2,3a,7-tetramethyl-5-phenylsulfanyl-hexahydro-benzo[1,3]dioxol-4-yl ester (82769-84-4,82769-85-5) → (1S,2R,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-12-oxo-13-aza-19-oxapentacyclo<9.7.02,10.03,8.011,15>nonadec-16-ene 6,7-acetonide (82770-11-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 15.0 g / m-chloroperbenzoic acid / CH₂Cl₂ / 1.) -35 deg C, 10 min, 2.) -35 deg C -> 25 deg C, 1 h

2: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / Heating

3: 1.) KDA / 1.) THF, 40 min, 2.) -25 deg C, 30 min

4: 1.) potassium tert-butoxide, 2.) ammoniua, lithium / 1.) tert-butyl alcohol, THF, 0 deg C, 5 min, 2.) -78 deg C, 1.5 h

6: 1.) 80percent m-chloroperbenzoic acid, sodium bicarbonate / 1.) methylene chloride, 0 deg C, 25 min, 2.) pyridine, 25 deg C, 3 h

7: 94 percent / methanesulfonic acid, trifluoroacetic acid / CH₂Cl₂ / 2 h / 25 °C

8: 78 percent / 1 h / 25 °C

9: 67 percent / toluene / 36 h / 110 °C

10: 96 percent / potassium tert-butoxide / H₂O; diethyl ether / 20 h / 25 °C

With methanesulfonic acid; Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; potassium tert-butylate; ammonia; lithium; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;

DOI:10.1021/ja00385a030

upstream raw materials:

(1S,2R,3S,5R,6R,7S,8R,11R,14R,15S,18R)-2-(benzoyloxy)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7-dihydroxy-5,7,16,17-tetramethyl-10,12-dioxo-13-azatetracyclo<9.7.0.0^3,8.0^11,15>octadec-16-ene 6,7-acetonide

(1S,2R,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-10-(benzoyloxy)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7-dihydroxy-5,7,16,17-tetramethyl-12-oxo-13-aza-19-oxapentacyclo<9.7.0^2,10.0^3,8.0^11,15>nonadec-16-ene 6,7-acetonide

(3aR,4R,5aS,6R,10aR)-6-Benzoyloxy-2,2,4,10b-tetramethyl-9-oxo-4,5,5a,6,9,10,10a,10b-octahydro-3aH-1,3-dioxa-cyclohepta[e]indene-8-carboxylic acid

C₂₄H₂₈O₇

Downstream raw materials:

(1S,3S,5R,6R,7S,8R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7-dihydroxy-5,7,16,17-tetramethyl-2,10,12-trioxo-13-azatetracyclo<9.7.0.0^3,8.0^11,15>octadec-16-ene 6,7-acetonide

(1S,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-2,12-dioxo-13-azatetracyclo<9.7.0.0^3,8.0^11,15>octadec-16-ene 6,7-acetonide

C₅₀H₆₃NO₇Si