Methyl 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-1-thio-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-1-thio-α-D-glucopyranoside
• CAS No.: 146934-31-8
• Molecular Formula: C₁₆H₁₈ClN₃O₅S
• Molecular Weight: 399.855
• Mol file: 146934-31-8.mol

Synonyms:Methyl 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property of Methyl 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-1-thio-α-D-glucopyranoside

There total 9 articles about Methyl 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-1-thio-α-D-glucopyranoside 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: 88.0%

Methyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside (146934-30-7) + chloroacetyl chloride (79-04-9) → Methyl 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-1-thio-α-D-glucopyranoside (146934-31-8)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; for 0.333333h; -50 to 0 deg C;

DOI:10.1016/S0040-4020(01)88331-9

Reference yield:

D-Mannose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → Methyl 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-1-thio-α-D-glucopyranoside (146934-31-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) glacial AcOH, Ac₂O, 30percent HBr/AcOH, 2) 2,4,6-trimethylpyridine / 1) 0 deg C to r.t., 4 h, 2) 14 h, r.t.

2: 32.4 percent / 1N aq. HCl / acetone / 0.08 h / 20 °C

3: 97.5 percent / pyridine / CH₂Cl₂ / -15 deg C to 5 deg C

4: 77 percent / NaN₃ / dimethylformamide / 0.67 h

5: trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 12 h / Heating

6: 82 percent / NaOMe / methanol / 3 h / Ambient temperature

7: 84 percent / 10-camphorsulfonic acid / acetonitrile / 3 h / Ambient temperature

8: 88 percent / pyridine / dimethylformamide / 0.33 h / -50 to 0 deg C

With pyridine; 2,4,6-trimethyl-pyridine; hydrogenchloride; sodium azide; trimethylsilyl trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; hydrogen bromide; sodium methylate; acetic anhydride; acetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)88331-9

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → Methyl 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-1-thio-α-D-glucopyranoside (146934-31-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / 10-camphorsulfonic acid / acetonitrile / 3 h / Ambient temperature

2: 88 percent / pyridine / dimethylformamide / 0.33 h / -50 to 0 deg C

With pyridine; (1S)-10-camphorsulfonic acid; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(01)88331-9

upstream raw materials:

Methyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside

chloroacetyl chloride

D-Mannose pentaacetate

benzaldehyde dimethyl acetal

Downstream raw materials:

2-Azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-glucopyranosyl chloride