phenyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: phenyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 204199-46-2
• Molecular Formula: C₃₆H₃₉N₃O₁₁S
• Molecular Weight: 721.785

Synonyms:phenyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property of phenyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

There total 13 articles about phenyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside 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:

Benzoic acid (2S,3R,4R,5S,6S)-4-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-3-azido-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-yloxy]-5-benzyloxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester → phenyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (204199-46-2)

Guidance literature:

With pyridine; thiourea; In N,N-dimethyl-formamide; at 23 ℃; for 24h; Yield given;

DOI:10.1002/(sici)1521-3773(19980202)37:1/2<138::aid-anie138>3.0.co;2-t

Reference yield:

phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (204199-43-9) → phenyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (204199-46-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 79 percent / HBF₄ / methanol; diethyl ether / 72 h / 23 °C

2: 10-camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 23 °C

3: 32 g / C₅H₅N / CH₂Cl₂ / 0.17 h / 0 °C

4: HBF₄ / methanol; CH₂Cl₂; diethyl ether / 0.5 h / 0 - 23 °C

5: C₅H₅N; 4-(dimethylamino)pyridine / 1 h / 0 - 23 °C

6: 19.7 g / thiourea / dimethylformamide; pyridine / 0.5 h / 23 °C

With pyridine; dmap; tetrafluoroboric acid; (1S)-10-camphorsulfonic acid; thiourea; In pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Deacetylation / 2: Cyclization / 3: Acylation / 4: methanolysis / 5: Acetylation / 6: dechloroacetylation;

DOI:10.1021/jo980660a

Reference yield:

phenyl 2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (204199-42-8) → phenyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (204199-46-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 63.5 percent / 2,6-di-tert-butyl-4-methylpyridine; 4-Angstroem molecular sieves; silver trifluoromethanesulfonate / CH₂Cl₂ / 2 h / -20 - 0 °C

2: 79 percent / HBF₄ / methanol; diethyl ether / 72 h / 23 °C

3: 10-camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 23 °C

4: 32 g / C₅H₅N / CH₂Cl₂ / 0.17 h / 0 °C

5: HBF₄ / methanol; CH₂Cl₂; diethyl ether / 0.5 h / 0 - 23 °C

6: C₅H₅N; 4-(dimethylamino)pyridine / 1 h / 0 - 23 °C

7: 19.7 g / thiourea / dimethylformamide; pyridine / 0.5 h / 23 °C

With pyridine; dmap; tetrafluoroboric acid; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; silver trifluoromethanesulfonate; thiourea; In pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Deacetylation / 3: Cyclization / 4: Acylation / 5: methanolysis / 6: Acetylation / 7: dechloroacetylation;

DOI:10.1021/jo980660a

upstream raw materials:

benzyl bromide

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

phenyl 4-O-benzyl-1-thio-α-L-rhamnopyranoside

phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

phenyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(4,6-di-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

phenyl [3,4,6-tri-O-benzyl-α-D-galactopyranosyl]-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

phenyl (3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-[4,6-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

phenyl [3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-(1->3)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

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 204199-46-2 phenyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Send

Send

Metric Ton KG G Pound L ML

Send

Send