methyl (prop-1-enyl 2,3-di-O-benzyl-4-O-chloroacetyl-α-D-glucopyranosid)uronate

Base Information

• Chemical Name: methyl (prop-1-enyl 2,3-di-O-benzyl-4-O-chloroacetyl-α-D-glucopyranosid)uronate
• CAS No.: 87906-99-8
• Molecular Formula: C₂₆H₂₉ClO₈
• Molecular Weight: 504.964
• Mol file: 87906-99-8.mol

Synonyms:methyl (prop-1-enyl 2,3-di-O-benzyl-4-O-chloroacetyl-α-D-glucopyranosid)uronate

Chemical Property of methyl (prop-1-enyl 2,3-di-O-benzyl-4-O-chloroacetyl-α-D-glucopyranosid)uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (prop-1-enyl 2,3-di-O-benzyl-4-O-chloroacetyl-α-D-glucopyranosid)uronate

There total 15 articles about methyl (prop-1-enyl 2,3-di-O-benzyl-4-O-chloroacetyl-α-D-glucopyranosid)uronate 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: 80.0%

methyl (prop-1-enyl 2,3-di-O-benzyl-α-D-glucopyranosid)uronate (87326-44-1) + chloroacetyl chloride (79-04-9) → methyl (prop-1-enyl 2,3-di-O-benzyl-4-O-chloroacetyl-α-D-glucopyranosid)uronate (87906-99-8)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/S0008-6215(00)90633-5

Reference yield:

allyl 4,6-O-benzylidene-α-D-glucopyranoside (93382-48-0) → methyl (prop-1-enyl 2,3-di-O-benzyl-4-O-chloroacetyl-α-D-glucopyranosid)uronate (87906-99-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 71 percent / sodium hydride / dimethylformamide / 0 °C

2: 100 percent / toluene-p-sulfonic acid / H₂O; methanol / 2 h / 80 °C

3: pyridine / 2 h / 80 °C

4: 80 °C / Heating

5: 24 g / aq. 80percent acetic acid / CH₂Cl₂ / Ambient temperature

6: 25 g / chromium trioxide, 3.5M sulfuric acid / acetone / 5 h / Ambient temperature

7: 1.) potassium tert-butoxide / 1.) methylsulfoxide, 1 h, 2.) ether

8: 80 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; chromium(VI) oxide; sulfuric acid; potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0008-6215(00)90633-5

Reference yield:

benzyl bromide (100-39-0) → methyl (prop-1-enyl 2,3-di-O-benzyl-4-O-chloroacetyl-α-D-glucopyranosid)uronate (87906-99-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 71 percent / sodium hydride / dimethylformamide / 0 °C

2: 100 percent / toluene-p-sulfonic acid / H₂O; methanol / 2 h / 80 °C

3: pyridine / 2 h / 80 °C

4: 80 °C / Heating

5: 24 g / aq. 80percent acetic acid / CH₂Cl₂ / Ambient temperature

6: 25 g / chromium trioxide, 3.5M sulfuric acid / acetone / 5 h / Ambient temperature

7: 1.) potassium tert-butoxide / 1.) methylsulfoxide, 1 h, 2.) ether

8: 80 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; chromium(VI) oxide; sulfuric acid; potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0008-6215(00)90633-5

upstream raw materials:

methyl (prop-1-enyl 2,3-di-O-benzyl-α-D-glucopyranosid)uronate

chloroacetyl chloride

allyl 4,6-O-benzylidene-α-D-glucopyranoside

benzyl bromide

Downstream raw materials:

methyl (2,3-di-O-benzyl-4-O-chloroacetyl-α-D-glucopyranosyl bromide)uronate

O-(methyl 2,3-di-O-benzyl-4-O-(chloroacetyl)-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

methyl 2,3-di-O-benzyl-4-O-chloroacetyl-D-glucopyranuronate