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-oxo-undecyl ester

Base Information

• Chemical Name: 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-oxo-undecyl ester
• CAS No.: 183947-42-4
• Molecular Formula: C₅₃H₈₂O₉S₂
• Molecular Weight: 927.361

Synonyms:

Chemical Property of 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-oxo-undecyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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-oxo-undecyl ester

There total 17 articles about 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-oxo-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:

benzyl bromide (100-39-0) → 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-oxo-undecyl ester (183947-42-4)

Guidance literature:

Multi-step reaction with 12 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

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

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,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-oxo-undecyl ester (183947-42-4)

Guidance literature:

Multi-step reaction with 11 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

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

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

Reference yield:

(1R,2S,3R)-3-benzyloxy-4-formyl-1-isopropyl-2-methoxybutyl benzoate (160238-70-0) → 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-oxo-undecyl ester (183947-42-4)

Guidance literature:

Multi-step reaction with 8 steps

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

2: 86 percent / trifluoromethanesulfonic acid / diethyl ether / 0.08 h / Ambient temperature

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

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

5: 99 percent / tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

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

7: 1.) 4-dimethylaminopyridine, 2.) DBU / 1.) CH₂Cl₂, RT, 12 h, 2.) CH₂Cl₂, from 0 to 20 deg C, 2 h

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

With dmap; lithium hydroxide; tellurium; sodium tetrahydroborate; diethylphosphoryl cyanide; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide;

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

upstream raw materials:

[2R,2(2R,3S,6R,8S,8(3S),9R),3E,6R,7S,9R,10S,11R]-11-acetoxy-9-benzyloxy-2-{3,9-dimethyl-8-[3-(2-methyl-1,3-dithian-2-yl)butyl]-1,7-dioxaspiro[5.5]undecan-2-yl}-10-methoxy-7-(4-methoxybenzyl)oxy-6,12-dimethyl-3-tridecen-5-one

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

Downstream raw materials:

tautomycin

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

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 183947-42-4 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-oxo-undecyl ester

Send

Send

Metric Ton KG G Pound L ML

Send

Send