Acetic acid (1R,2S,3R,5S,6R,7S,10R)-3-benzyloxy-10-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-((S)-3-methyl-4-oxo-pentyl)-1,7-dioxa-spiro[5.5]undec-2-yl]-1-isopropyl-2-methoxy-5-(4-methoxy-benzyloxy)-6-methyl-7-triethylsilanyloxy-undecyl ester

Base Information

• Chemical Name: Acetic acid (1R,2S,3R,5S,6R,7S,10R)-3-benzyloxy-10-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-((S)-3-methyl-4-oxo-pentyl)-1,7-dioxa-spiro[5.5]undec-2-yl]-1-isopropyl-2-methoxy-5-(4-methoxy-benzyloxy)-6-methyl-7-triethylsilanyloxy-undecyl ester
• CAS No.: 183947-45-7
• Molecular Formula: C₅₆H₉₂O₁₀Si
• Molecular Weight: 953.426

Synonyms:Acetic acid (1R,2S,3R,5S,6R,7S,10R)-3-benzyloxy-10-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-((S)-3-methyl-4-oxo-pentyl)-1,7-dioxa-spiro[5.5]undec-2-yl]-1-isopropyl-2-methoxy-5-(4-methoxy-benzyloxy)-6-methyl-7-triethylsilanyloxy-undecyl ester

Chemical Property of Acetic acid (1R,2S,3R,5S,6R,7S,10R)-3-benzyloxy-10-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-((S)-3-methyl-4-oxo-pentyl)-1,7-dioxa-spiro[5.5]undec-2-yl]-1-isopropyl-2-methoxy-5-(4-methoxy-benzyloxy)-6-methyl-7-triethylsilanyloxy-undecyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of Acetic acid (1R,2S,3R,5S,6R,7S,10R)-3-benzyloxy-10-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-((S)-3-methyl-4-oxo-pentyl)-1,7-dioxa-spiro[5.5]undec-2-yl]-1-isopropyl-2-methoxy-5-(4-methoxy-benzyloxy)-6-methyl-7-triethylsilanyloxy-undecyl ester

There total 20 articles about Acetic acid (1R,2S,3R,5S,6R,7S,10R)-3-benzyloxy-10-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-((S)-3-methyl-4-oxo-pentyl)-1,7-dioxa-spiro[5.5]undec-2-yl]-1-isopropyl-2-methoxy-5-(4-methoxy-benzyloxy)-6-methyl-7-triethylsilanyloxy-undecyl 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: 81.0%

Acetic acid (1R,2S,3R,5S,6R,10R)-3-benzyloxy-10-{(2S,3S,6R,8S,9R)-3,9-dimethyl-8-[(S)-3-(2-methyl-[1,3]dithian-2-yl)-butyl]-1,7-dioxa-spiro[5.5]undec-2-yl}-1-isopropyl-2-methoxy-5-(4-methoxy-benzyloxy)-6-methyl-7-triethylsilanyloxy-undecyl ester → Acetic acid (1R,2S,3R,5S,6R,7S,10R)-3-benzyloxy-10-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-((S)-3-methyl-4-oxo-pentyl)-1,7-dioxa-spiro[5.5]undec-2-yl]-1-isopropyl-2-methoxy-5-(4-methoxy-benzyloxy)-6-methyl-7-triethylsilanyloxy-undecyl ester (183947-45-7)

Guidance literature:

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; silver nitrate; In acetonitrile; at 0 ℃; for 0.166667h;

DOI:10.1016/0040-4020(96)00811-3

Reference yield:

benzyl bromide (100-39-0) → Acetic acid (1R,2S,3R,5S,6R,7S,10R)-3-benzyloxy-10-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-((S)-3-methyl-4-oxo-pentyl)-1,7-dioxa-spiro[5.5]undec-2-yl]-1-isopropyl-2-methoxy-5-(4-methoxy-benzyloxy)-6-methyl-7-triethylsilanyloxy-undecyl ester (183947-45-7)

Guidance literature:

Multi-step reaction with 15 steps

1: 100 percent / NaH / tetrahydrofuran; dimethylformamide / 12 h / Ambient temperature

2: 81 percent / BF₃*Et₂O / CH₂Cl₂ / 24 h / Ambient temperature

3: DMAP, pyridine / CH₂Cl₂ / 72 h / Ambient temperature

4: NBS, H₂O / acetone / 0.17 h / -23 °C

5: 1.) n-Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 1.5 h

6: 86 percent / trifluoromethanesulfonic acid / diethyl ether / 0.08 h / Ambient temperature

7: LiOH*H₂O, aq. H₂O₂ / tetrahydrofuran / 11 h / Ambient temperature

8: diethylphosphoryl cyanide, Et₃N / dimethylformamide / 2 h / Ambient temperature

9: 99 percent / tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

10: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h

11: 1.) 4-dimethylaminopyridine, 2.) DBU / 1.) CH₂Cl₂, RT, 12 h, 2.) CH₂Cl₂, from 0 to 20 deg C, 2 h

12: NaBH₄, Te, AcOH / ethanol / 4 h / Ambient temperature

13: L-Selectride / tetrahydrofuran / -80 - -30 °C

14: 89 percent / i-Pr₂NEt / CH₂Cl₂ / 0.67 h / -40 °C

15: 81 percent / NBS, AgNO₃, 2,4,6-collidine / acetonitrile / 0.17 h / 0 °C

With pyridine; 2,4,6-trimethyl-pyridine; dmap; lithium hydroxide; tellurium; sodium tetrahydroborate; N-Bromosuccinimide; diethylphosphoryl cyanide; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; water; dihydrogen peroxide; L-Selectride; sodium hydride; silver nitrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/0040-4020(96)00811-3

Reference yield:

(2R,3S,4R,6S)-4-benzyloxy-2-isopropyl-3,6-dimethoxy-3,4,5,6-tetrahydro-2H-pyran (160238-68-6) → Acetic acid (1R,2S,3R,5S,6R,7S,10R)-3-benzyloxy-10-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-((S)-3-methyl-4-oxo-pentyl)-1,7-dioxa-spiro[5.5]undec-2-yl]-1-isopropyl-2-methoxy-5-(4-methoxy-benzyloxy)-6-methyl-7-triethylsilanyloxy-undecyl ester (183947-45-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 81 percent / BF₃*Et₂O / CH₂Cl₂ / 24 h / Ambient temperature

2: DMAP, pyridine / CH₂Cl₂ / 72 h / Ambient temperature

3: NBS, H₂O / acetone / 0.17 h / -23 °C

4: 1.) n-Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 1.5 h

5: 86 percent / trifluoromethanesulfonic acid / diethyl ether / 0.08 h / Ambient temperature

6: LiOH*H₂O, aq. H₂O₂ / tetrahydrofuran / 11 h / Ambient temperature

7: diethylphosphoryl cyanide, Et₃N / dimethylformamide / 2 h / Ambient temperature

8: 99 percent / tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

9: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h

10: 1.) 4-dimethylaminopyridine, 2.) DBU / 1.) CH₂Cl₂, RT, 12 h, 2.) CH₂Cl₂, from 0 to 20 deg C, 2 h

11: NaBH₄, Te, AcOH / ethanol / 4 h / Ambient temperature

12: L-Selectride / tetrahydrofuran / -80 - -30 °C

13: 89 percent / i-Pr₂NEt / CH₂Cl₂ / 0.67 h / -40 °C

14: 81 percent / NBS, AgNO₃, 2,4,6-collidine / acetonitrile / 0.17 h / 0 °C

With pyridine; 2,4,6-trimethyl-pyridine; dmap; lithium hydroxide; tellurium; sodium tetrahydroborate; N-Bromosuccinimide; diethylphosphoryl cyanide; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; water; dihydrogen peroxide; L-Selectride; silver nitrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/0040-4020(96)00811-3

upstream raw materials:

benzyl bromide

(2R,3S,4R,6S)-4-benzyloxy-2-isopropyl-3,6-dimethoxy-3,4,5,6-tetrahydro-2H-pyran

(1R,2S,3R)-3-benzyloxy-4-formyl-1-isopropyl-2-methoxybutyl benzoate

<2S,2<2R,3S,6R,8S,8(3S),9R>>-2-<3,9-dimethyl-8-<3-(2-methyl-1,3-dithian-2-yl)butyl>-1,7-dioxaspiro<5.5>undecane-2-yl>-1-propanal

Downstream raw materials:

tautomycin

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