methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate

Base Information

• Chemical Name: methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate
• CAS No.: 615543-18-5
• Molecular Formula: C₂₆H₃₂Cl₃NO₁₀
• Molecular Weight: 624.9

Synonyms:methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate

Chemical Property of methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate

There total 27 articles about methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate 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:

trichloroacetonitrile (545-06-2) + (2R,3S,4S,5R)-4-Benzyloxy-5-(2,2-dimethyl-propionyloxy)-6-hydroxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester → methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate (615543-18-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1021/jo0340760

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate (615543-18-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium periodate; silica gel / CH₂Cl₂; H₂O / 1.5 h

2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C

2.2: tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C

3.1: CuCl₂; CuO / H₂O; CH₂Cl₂ / 0.08 h / 20 °C

3.2: 437 mg / K₂CO₃ / CH₂Cl₂; methanol / 1.5 h / 20 °C

4.1: trifluoroacetic acid / H₂O / 0.58 h / 20 °C

5.1: (+)-camphorsulfonic acid / dimethylformamide / 3 h / 0 °C

5.2: 199 mg / Dowex 50W acidic resin / methanol / 0.33 h / 20 °C

6.1: 98 percent / DIPC; DMAP / CH₂Cl₂ / 11 h / 20 °C

7.1: trifluoroacetic acid / H₂O / 0.25 h / 20 °C

8.1: imidazole / CH₂Cl₂ / 41 h / -20 °C

8.2: 588 mg / DMAP / CH₂Cl₂ / 48 h / 20 °C

9.1: HF*pyridine / tetrahydrofuran / 28 h / 20 °C

10.1: 398 mg / DBU / CH₂Cl₂ / 0.5 h / 0 - 20 °C

With 1H-imidazole; dmap; sodium periodate; n-butyllithium; bis-2-propyl carbonate; silica gel; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; trifluoroacetic acid; copper(II) oxide; copper dichloride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0340760

Reference yield:

benzyl bromide (100-39-0) → methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate (615543-18-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: NaH; tetrabutylammonium iodide / tetrahydrofuran / 14 h / 20 °C

2.1: 17.8 g / acetic acid / H₂O / 16 h / 20 °C

3.1: sodium periodate; silica gel / CH₂Cl₂; H₂O / 1.5 h

4.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C

4.2: tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C

5.1: CuCl₂; CuO / H₂O; CH₂Cl₂ / 0.08 h / 20 °C

5.2: 437 mg / K₂CO₃ / CH₂Cl₂; methanol / 1.5 h / 20 °C

6.1: trifluoroacetic acid / H₂O / 0.58 h / 20 °C

7.1: (+)-camphorsulfonic acid / dimethylformamide / 3 h / 0 °C

7.2: 199 mg / Dowex 50W acidic resin / methanol / 0.33 h / 20 °C

8.1: 98 percent / DIPC; DMAP / CH₂Cl₂ / 11 h / 20 °C

9.1: trifluoroacetic acid / H₂O / 0.25 h / 20 °C

10.1: imidazole / CH₂Cl₂ / 41 h / -20 °C

10.2: 588 mg / DMAP / CH₂Cl₂ / 48 h / 20 °C

11.1: HF*pyridine / tetrahydrofuran / 28 h / 20 °C

12.1: 398 mg / DBU / CH₂Cl₂ / 0.5 h / 0 - 20 °C

With 1H-imidazole; dmap; sodium periodate; n-butyllithium; bis-2-propyl carbonate; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridine hydrogenfluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; trifluoroacetic acid; copper(II) oxide; copper dichloride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0340760

upstream raw materials:

trichloroacetonitrile

2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal

2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-D-xylose di(ethylthio)acetal

C₂₆H₃₈O₇S₂

Downstream raw materials:

(2R,3S,4S,5R,6R)-4-Benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-(4-oxo-pentanoyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3S,4S,5R,6R)-4-Benzyloxy-6-(5-benzyloxycarbonylamino-pentyloxy)-5-(2,2-dimethyl-propionyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

C₆₈H₈₄N₄O₂₄

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 615543-18-5 methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosiduronate trichloroacetimidate

Send

Send

Metric Ton KG G Pound L ML

Send

Send