1-O-p-toluenesulfonyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol

Base Information

• Chemical Name: 1-O-p-toluenesulfonyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol
• CAS No.: 108811-06-9
• Molecular Formula: C₄₄H₄₈O₁₀S
• Molecular Weight: 768.925
• Mol file: 108811-06-9.mol

Synonyms:1-O-p-toluenesulfonyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol

Chemical Property of 1-O-p-toluenesulfonyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-p-toluenesulfonyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol

There total 8 articles about 1-O-p-toluenesulfonyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol 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: 59.0%

3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol (65751-67-9) + p-toluenesulfonyl chloride (98-59-9) → 1-O-p-toluenesulfonyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol (108811-06-9)

Guidance literature:

In pyridine; at 5 - 10 ℃; for 16h;

Reference yield:

D-glucose 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) → 1-O-p-toluenesulfonyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol (108811-06-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / tin(IV) chloride / CH₂Cl₂ / 16 h / 20 °C

2: 1 N sodium methoxide / methanol / 16 h / 20 °C

3: 90.2 percent / 50percent sodium hydride / dimethylformamide; paraffin / 16 h / 20 °C

4: 77 percent / calcium carbonate, mercuric(II) chloride / acetonitrile; H₂O / 5 h / Heating

5: thionyl chloride / dimethylformamide; 1,2-dichloro-ethane / 16 h / 20 °C

6: 48.8 percent / tetrabutylammonium chloride, N_.N-diisopropylethylamine / 1,2-dichloro-ethane / 16 h / 85 - 95 °C

7: 94 percent / 16 h / 20 °C

8: 59 percent / pyridine / 16 h / 5 - 10 °C

With thionyl chloride; tetrabutyl-ammonium chloride; sodium methylate; tin(IV) chloride; sodium hydride; N-ethyl-N,N-diisopropylamine; calcium carbonate; mercury dichloride; In pyridine; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; paraffin;

Reference yield:

tetra-O-benzyl glucopyranosyl chloride (25320-59-6) → 1-O-p-toluenesulfonyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol (108811-06-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 48.8 percent / tetrabutylammonium chloride, N_.N-diisopropylethylamine / 1,2-dichloro-ethane / 16 h / 85 - 95 °C

2: 94 percent / 16 h / 20 °C

3: 59 percent / pyridine / 16 h / 5 - 10 °C

With tetrabutyl-ammonium chloride; N-ethyl-N,N-diisopropylamine; In pyridine; 1,2-dichloro-ethane;

upstream raw materials:

3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol

p-toluenesulfonyl chloride

D-glucose pentaacetate

tetra-O-benzyl glucopyranosyl chloride

Downstream raw materials:

1-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-3-deoxy-2(R)-glycerol

1,2-anhydro-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol