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

Base Information

• Chemical Name: 2,3-anhydro-1-O-<2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranosyl>-sn-glycerol
• CAS No.: 84276-57-3
• Molecular Formula: C₆₄H₆₈O₁₂
• Molecular Weight: 1029.24
• Mol file: 84276-57-3.mol

Synonyms:2,3-anhydro-1-O-<2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranosyl>-sn-glycerol

Chemical Property of 2,3-anhydro-1-O-<2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranosyl>-sn-glycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-anhydro-1-O-<2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranosyl>-sn-glycerol

There total 19 articles about 2,3-anhydro-1-O-<2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-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: 87.0%

1-O-benzoyl-2-O-p-toluenesulfonyl-3-O-<2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranosyl>-sn-glycerol → 2,3-anhydro-1-O-<2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranosyl>-sn-glycerol (84276-57-3)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; at 0 ℃; for 6h;

Reference yield:

allyl β-D-glucopyranoside (2595-07-5,7464-56-4,34384-79-7,41308-76-3,48149-72-0,48149-74-2,85249-43-0,119479-69-5,821794-45-0) → 2,3-anhydro-1-O-<2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranosyl>-sn-glycerol (84276-57-3)

Guidance literature:

Multi-step reaction with 17 steps

1: 91.1 percent / p-toluenesulfonic acid / dimethylformamide / 2 h / 60 °C / 20 Torr

2: 71 percent / 50percent sodium hydride / dimethylformamide; paraffin / 16 h / 20 °C

3: 97.6 percent / aq. acetic acid / 6 h / 100 °C

4: 1.) bis(tri-n-butyltin)oxide; 2.) tetrabutylammonium bromide / 1.) toluene, 16 h, reflux; 2.) toluene, 100 deg C, 16 h

5: 94.5 percent / pyridine / 20 °C

6: 1.) palladium(II) chloride, sodium acetate; 2.) thionyl chloride, dimethylformamide / 1.) aq. acetic acid, 60 deg C, 14 h; 2.) dichloroethane, 20 deg C, 16 h

7: 68.1 percent / tetrabutylammonium chloride, N,N-diisopropylethylamine / 1,2-dichloro-ethane / 16 h / 80 - 90 °C

8: 65.5 percent / camphorsulfonic acid / methanol / 24 h / 20 °C

9: 98.3 percent / p-toluenesulfonic acid / dimethylformamide / 2 h / 40 °C / 20 Torr

10: 1 N sodium methoxide / methanol / 16 h / 20 °C

11: 92.5 percent / molecular sieves 4A, silver trifluoromethanesulfonate / 1,2-dichloro-ethane / 2 h

12: 93.5 percent / 1 N sodium methoxide / methanol / 16 h / 20 °C

13: 64.9 percent / 50percent sodium hydride / dimethylformamide; paraffin / 16 h / 20 °C

14: 87.2 percent / p-toluenesulfonic acid / methanol / 16 h / 20 °C

15: 63.6 percent / pyridine / 16 h / 0 - 5 °C

16: 89.5 percent / 4-dimethylaminopyridine / pyridine / 12 h / 20 °C

17: 87 percent / 0.5 N sodium methoxide / methanol; tetrahydrofuran / 6 h / 0 °C

With pyridine; thionyl chloride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutylammomium bromide; tetrabutyl-ammonium chloride; sodium methylate; sodium acetate; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; bis(tri-n-butyltin)oxide; palladium dichloride; dmap; In tetrahydrofuran; pyridine; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide; paraffin;

Reference yield:

4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride (61236-94-0) → 2,3-anhydro-1-O-<2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranosyl>-sn-glycerol (84276-57-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 68.1 percent / tetrabutylammonium chloride, N,N-diisopropylethylamine / 1,2-dichloro-ethane / 16 h / 80 - 90 °C

2: 65.5 percent / camphorsulfonic acid / methanol / 24 h / 20 °C

3: 98.3 percent / p-toluenesulfonic acid / dimethylformamide / 2 h / 40 °C / 20 Torr

4: 1 N sodium methoxide / methanol / 16 h / 20 °C

5: 92.5 percent / molecular sieves 4A, silver trifluoromethanesulfonate / 1,2-dichloro-ethane / 2 h

6: 93.5 percent / 1 N sodium methoxide / methanol / 16 h / 20 °C

7: 64.9 percent / 50percent sodium hydride / dimethylformamide; paraffin / 16 h / 20 °C

8: 87.2 percent / p-toluenesulfonic acid / methanol / 16 h / 20 °C

9: 63.6 percent / pyridine / 16 h / 0 - 5 °C

10: 89.5 percent / 4-dimethylaminopyridine / pyridine / 12 h / 20 °C

11: 87 percent / 0.5 N sodium methoxide / methanol; tetrahydrofuran / 6 h / 0 °C

With 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl-ammonium chloride; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; dmap; In tetrahydrofuran; pyridine; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide; paraffin;

upstream raw materials:

Benzoic acid (S)-3-[(2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-(toluene-4-sulfonyloxy)-propyl ester

allyl β-D-glucopyranoside

4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl chloride

benzyl bromide

Downstream raw materials:

1-O-(4-O-β-D-glucopyranosyl-α-D-glucopyranosyl)-3-deoxy-2(S)-glycerol