N-(benzyl)-N-benzyloxycarbonyl-5-aminopentyl (2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-3-O-benzyl-α-L-idopyranosiduronic acid

Base Information

• Chemical Name: N-(benzyl)-N-benzyloxycarbonyl-5-aminopentyl (2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-3-O-benzyl-α-L-idopyranosiduronic acid
• CAS No.: 945224-50-0
• Molecular Formula: C₅₃H₆₀N₄O₁₃
• Molecular Weight: 961.078

Synonyms:N-(benzyl)-N-benzyloxycarbonyl-5-aminopentyl (2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-3-O-benzyl-α-L-idopyranosiduronic acid

Chemical Property of N-(benzyl)-N-benzyloxycarbonyl-5-aminopentyl (2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-3-O-benzyl-α-L-idopyranosiduronic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(benzyl)-N-benzyloxycarbonyl-5-aminopentyl (2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-3-O-benzyl-α-L-idopyranosiduronic acid

There total 20 articles about N-(benzyl)-N-benzyloxycarbonyl-5-aminopentyl (2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-3-O-benzyl-α-L-idopyranosiduronic acid 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: 85.0%

C61H72O15N4 (945224-49-7) → N-(benzyl)-N-benzyloxycarbonyl-5-aminopentyl (2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-3-O-benzyl-α-L-idopyranosiduronic acid (945224-50-0)

Guidance literature:

C₆₁H₇₂O₁₅N₄; With lithium hydroxide; water; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 16h;

With methanol; potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 16h; Further stages.;

DOI:10.1002/chem.200700141

Reference yield:

2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal (945224-35-1) → N-(benzyl)-N-benzyloxycarbonyl-5-aminopentyl (2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-3-O-benzyl-α-L-idopyranosiduronic acid (945224-50-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 90 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 0.08 h

2.1: 94 percent / sulfur trioxide pyridine complex; DIPEA; dimethyl sulfoxide / CH₂Cl₂ / 0.25 h / 0 °C

3.1: MgBr₂*OEt₂ / CH₂Cl₂ / 20 °C

3.2: 73 percent / hydrazine acetate / CH₂Cl₂; methanol / 12 h / 20 °C

4.1: acetyl chloride / toluene / 0 - 20 °C

4.2: 70 percent / water / toluene / 0 - 20 °C

5.1: 4-dimethylaminopyridine; N,N'-diisopropylcarbodiimide / CH₂Cl₂ / 2.5 h / 0 °C

6.1: bis(trifluoroacetoxy)iodobenzene; water; NaHCO₃ / acetonitrile / 0.5 h / 20 °C

6.2: trifluoroacetic acid / H₂O / 0.5 h / 50 °C

7.1: 461 mg / DBU / CH₂Cl₂ / 0.5 h / 0 - 20 °C

8.1: TMSOTf / CH₂Cl₂ / 0.5 h / -20 - -10 °C

9.1: 96 percent / pyridine; acetic acid; hydrazine monohydrate / CH₂Cl₂ / 1.5 h / 20 °C

10.1: 81 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -25 °C

11.1: H₂O₂; LiOH; H₂O / tetrahydrofuran / 16 h / 20 °C

11.2: 85 percent / aq. KOH; MeOH / tetrahydrofuran / 16 h / 20 °C

With pyridine; triethylsilane; dmap; lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; water; dihydrogen peroxide; sulfur trioxide pyridine complex; sodium hydrogencarbonate; hydrazine hydrate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; acetyl chloride; trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene; magnesium bromide; diisopropyl-carbodiimide; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 2.1: Parikh-Doering oxidation / 4.1: Pinner reaction;

DOI:10.1002/chem.200700141

Reference yield:

2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-D-xylose di(ethylthio)acetal (945224-36-2) → N-(benzyl)-N-benzyloxycarbonyl-5-aminopentyl (2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-3-O-benzyl-α-L-idopyranosiduronic acid (945224-50-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 94 percent / sulfur trioxide pyridine complex; DIPEA; dimethyl sulfoxide / CH₂Cl₂ / 0.25 h / 0 °C

2.1: MgBr₂*OEt₂ / CH₂Cl₂ / 20 °C

2.2: 73 percent / hydrazine acetate / CH₂Cl₂; methanol / 12 h / 20 °C

3.1: acetyl chloride / toluene / 0 - 20 °C

3.2: 70 percent / water / toluene / 0 - 20 °C

4.1: 4-dimethylaminopyridine; N,N'-diisopropylcarbodiimide / CH₂Cl₂ / 2.5 h / 0 °C

5.1: bis(trifluoroacetoxy)iodobenzene; water; NaHCO₃ / acetonitrile / 0.5 h / 20 °C

5.2: trifluoroacetic acid / H₂O / 0.5 h / 50 °C

6.1: 461 mg / DBU / CH₂Cl₂ / 0.5 h / 0 - 20 °C

7.1: TMSOTf / CH₂Cl₂ / 0.5 h / -20 - -10 °C

8.1: 96 percent / pyridine; acetic acid; hydrazine monohydrate / CH₂Cl₂ / 1.5 h / 20 °C

9.1: 81 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -25 °C

10.1: H₂O₂; LiOH; H₂O / tetrahydrofuran / 16 h / 20 °C

10.2: 85 percent / aq. KOH; MeOH / tetrahydrofuran / 16 h / 20 °C

With pyridine; dmap; lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; water; dihydrogen peroxide; sulfur trioxide pyridine complex; sodium hydrogencarbonate; hydrazine hydrate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; acetyl chloride; bis-[(trifluoroacetoxy)iodo]benzene; magnesium bromide; diisopropyl-carbodiimide; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 1.1: Parikh-Doering oxidation / 3.1: Pinner reaction;

DOI:10.1002/chem.200700141

upstream raw materials:

C₆₁H₇₂O₁₅N₄

(2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-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

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

Downstream raw materials:

C₅₃H₆₀O₁₉N₄S₂

C₅₃H₆₂O₁₉N₂S₂

C₅₅H₆₄O₂₀N₂S₂

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 945224-50-0 N-(benzyl)-N-benzyloxycarbonyl-5-aminopentyl (2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-3-O-benzyl-α-L-idopyranosiduronic acid

Send

Send

Metric Ton KG G Pound L ML

Send

Send