4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-methoxy-1-methyl-8-(3-methyl-[1,2,4]oxadiazol-5-yl)-10-thioxo-13-trityloxymethyl-8,9,10,11,12,13-hexahydro-5H,7H-14-oxa-6-thia-9-aza-benzocyclotridecen-15-one

Base Information

Chemical Name:4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-methoxy-1-methyl-8-(3-methyl-[1,2,4]oxadiazol-5-yl)-10-thioxo-13-trityloxymethyl-8,9,10,11,12,13-hexahydro-5H,7H-14-oxa-6-thia-9-aza-benzocyclotridecen-15-one
CAS No.:676347-39-0
Molecular Formula:C₄₇H₅₇N₃O₆S₂Si
Molecular Weight:852.204
Hs Code.:

4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-methoxy-1-methyl-8-(3-methyl-[1,2,4]oxadiazol-5-yl)-10-thioxo-13-trityloxymethyl-8,9,10,11,12,13-hexahydro-5<i>H</i>,7<i>H</i>-14-oxa-6-thia-9-aza-benzocyclotridecen-15-one

Synonyms:4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-methoxy-1-methyl-8-(3-methyl-[1,2,4]oxadiazol-5-yl)-10-thioxo-13-trityloxymethyl-8,9,10,11,12,13-hexahydro-5H,7H-14-oxa-6-thia-9-aza-benzocyclotridecen-15-one

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Chemical Property of 4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-methoxy-1-methyl-8-(3-methyl-[1,2,4]oxadiazol-5-yl)-10-thioxo-13-trityloxymethyl-8,9,10,11,12,13-hexahydro-5H,7H-14-oxa-6-thia-9-aza-benzocyclotridecen-15-one

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Technology Process of 4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-methoxy-1-methyl-8-(3-methyl-[1,2,4]oxadiazol-5-yl)-10-thioxo-13-trityloxymethyl-8,9,10,11,12,13-hexahydro-5H,7H-14-oxa-6-thia-9-aza-benzocyclotridecen-15-one

There total 15 articles about 4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-methoxy-1-methyl-8-(3-methyl-[1,2,4]oxadiazol-5-yl)-10-thioxo-13-trityloxymethyl-8,9,10,11,12,13-hexahydro-5H,7H-14-oxa-6-thia-9-aza-benzocyclotridecen-15-one 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:

: 36326-38-2,64520-58-7,91057-97-5,91926-90-8,104321-63-3,124818-64-0,128525-67-7,128525-69-9,104321-62-2,917877-01-1
ethyl (E)-3-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate

: 676347-39-0
4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-methoxy-1-methyl-8-(3-methyl-[1,2,4]oxadiazol-5-yl)-10-thioxo-13-trityloxymethyl-8,9,10,11,12,13-hexahydro-5H,7H-14-oxa-6-thia-9-aza-benzocyclotridecen-15-one

Guidance literature:: Multi-step reaction with 8 steps

1: H₂ / Pd/C / ethyl acetate / 1 h / atmospheric pressure

2: KOH / methanol / 1.5 h / 40 °C

3: 79 percent / EDC / acetonitrile / 4 h / 0 °C

4: aq. AcOH / 0.33 h / 60 °C

5: 8.5 g / pyridine / 21 h / 20 °C

6: morpholine; Pd(PPh₃)4 / tetrahydrofuran / 2 h / 0 °C

7: PPh₃; DEAD / tetrahydrofuran / 16 h / 20 °C

8: Lawesson's reagent / toluene / 0.5 h / 80 °C

With Lawessons reagent; morpholine; pyridine; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; toluene; acetonitrile; 7: Mitsunobu conditions;
DOI:10.1021/jm0310232

Reference yield:

: 52344-94-2
methyl 3,5-dimethoxy-2-methylbenzoate

: 676347-39-0
4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-methoxy-1-methyl-8-(3-methyl-[1,2,4]oxadiazol-5-yl)-10-thioxo-13-trityloxymethyl-8,9,10,11,12,13-hexahydro-5H,7H-14-oxa-6-thia-9-aza-benzocyclotridecen-15-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: 92 percent / POCl₃ / CH₂Cl₂ / 72 h / 40 °C

2.1: 86 percent / BCl₃ / CH₂Cl₂ / 4.5 h / 20 °C

3.1: 98 percent / aq. KOH / 0.5 h / 75 °C

4.1: N,N,N',N'-tetramethylguanidine / dimethylformamide / 0.5 h

4.2: 86 percent / dimethylformamide / 3 h

5.1: 90 percent / Et₃N / dimethylformamide / 6 h

6.1: 69 percent / TFA; Et₃SiH / CH₂Cl₂ / 18 h / 0 °C

7.1: 79 percent / EDC / acetonitrile / 4 h / 0 °C

8.1: aq. AcOH / 0.33 h / 60 °C

9.1: 8.5 g / pyridine / 21 h / 20 °C

10.1: morpholine; Pd(PPh₃)4 / tetrahydrofuran / 2 h / 0 °C

11.1: PPh₃; DEAD / tetrahydrofuran / 16 h / 20 °C

12.1: Lawesson's reagent / toluene / 0.5 h / 80 °C

With Lawessons reagent; morpholine; pyridine; triethylsilane; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trichloride; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; trichlorophosphate; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Vilsmeyer formylation / 11.1: Mitsunobu conditions;
DOI:10.1021/jm0310232

Reference yield:

: 67373-56-2
chlorodimethyl(1,1,2-trimethylpropyl)silane

: 676347-39-0
4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-methoxy-1-methyl-8-(3-methyl-[1,2,4]oxadiazol-5-yl)-10-thioxo-13-trityloxymethyl-8,9,10,11,12,13-hexahydro-5H,7H-14-oxa-6-thia-9-aza-benzocyclotridecen-15-one

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / Et₃N / dimethylformamide / 6 h

2: 69 percent / TFA; Et₃SiH / CH₂Cl₂ / 18 h / 0 °C

3: 79 percent / EDC / acetonitrile / 4 h / 0 °C

4: aq. AcOH / 0.33 h / 60 °C

5: 8.5 g / pyridine / 21 h / 20 °C

6: morpholine; Pd(PPh₃)4 / tetrahydrofuran / 2 h / 0 °C

7: PPh₃; DEAD / tetrahydrofuran / 16 h / 20 °C

8: Lawesson's reagent / toluene / 0.5 h / 80 °C

With Lawessons reagent; morpholine; pyridine; triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 7: Mitsunobu conditions;
DOI:10.1021/jm0310232