benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid

Base Information

• Chemical Name: benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid
• CAS No.: 95451-84-6
• Molecular Formula: C₂₂H₂₇NO₆
• Molecular Weight: 401.459
• Mol file: 95451-84-6.mol

Synonyms:benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid

Chemical Property of benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid

There total 13 articles about benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid 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: 86.0%

Benzyl-2-acetamido-3-O-benzyl-4,6-O-benzyliden-2-desoxy-α-D-mannopyranosid (14040-20-1,14146-26-0,75869-81-7,97604-75-6,119943-67-8) → benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid (95451-84-6)

Guidance literature:

With trifluoroacetic acid; In methanol; water; at 60 ℃; for 0.5h;

DOI:10.1016/0008-6215(85)85193-4

Reference yield:

3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide (95451-93-7) → benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid (95451-84-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / molecular sieves 4 Angstroem / HgBr₂ / CH₂Cl₂ / 2 h / Ambient temperature

2: 98 percent / sodiummethoxide / methanol / 4 h / Ambient temperature

3: 78 percent / triethylamine, H₂S-gas / pyridine; H₂O / 2 h / Ambient temperature

4: 88 percent / methanol / 0.5 h

5: 45 percent / p-toluenesulfonic acid / dimethylformamide / 0.5 h / 60 °C

6: 94 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 6 h / Ambient temperature

7: 86 percent / trifluoroacetic acid / methanol; H₂O / 0.5 h / 60 °C

With barium dihydroxide; 4 A molecular sieve; hydrogen sulfide; sodium methylate; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; barium(II) oxide; mercury dibromide; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(85)85193-4

Reference yield:

D-glucal triacetate (2873-29-2) → benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid (95451-84-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) (NH₄)23)6>, NaN₃ / 1.) EtOAc, CH₃CN, -40 deg C, 6 d; 2.) glacial acetic acid, 100 deg C, 1 h

2: 98 percent / TiBr₄ / CH₂Cl₂; ethyl acetate / 144 h

3: 84 percent / molecular sieves 4 Angstroem / HgBr₂ / CH₂Cl₂ / 2 h / Ambient temperature

4: 98 percent / sodiummethoxide / methanol / 4 h / Ambient temperature

5: 78 percent / triethylamine, H₂S-gas / pyridine; H₂O / 2 h / Ambient temperature

6: 88 percent / methanol / 0.5 h

7: 45 percent / p-toluenesulfonic acid / dimethylformamide / 0.5 h / 60 °C

8: 94 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 6 h / Ambient temperature

9: 86 percent / trifluoroacetic acid / methanol; H₂O / 0.5 h / 60 °C

With barium dihydroxide; sodium azide; ammonium cerium(IV) nitrate; 4 A molecular sieve; hydrogen sulfide; sodium methylate; titanium(IV) bromide; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; barium(II) oxide; mercury dibromide; In pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(85)85193-4

upstream raw materials:

acetic anhydride

(2R,3S,4R,5S,6S)-5-Amino-4,6-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-ol

Benzyl-2-acetamido-3-O-benzyl-4,6-O-benzyliden-2-desoxy-α-D-mannopyranosid

Benzyl-2-amino-2-desoxy-α-D-mannopyranosid

Downstream raw materials:

(Benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid)uronsaeure

Refernces

• 1、 Paulsen, Hans,Lorentzen, Jens Peter,Kutschker, Wolfram. "ERPROBTE SYNTHESE VON 2-AZIDO-2-DESOXY-D-MANNOSE UND 2-AZIDO-2-DESOXY-D-MANNURONSAEURE ALS BAUSTEIN ZUM AUFBAU VON BAKTERIEN-POLYSACCHARID-SEQUENZEN". . p. 153 - 176. Retrieved 2007/10/02.