benzyl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

Base Information

• Chemical Name: benzyl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside
• CAS No.: 93661-30-4
• Molecular Formula: C₄₆H₅₆O₁₆
• Molecular Weight: 864.941
• Mol file: 93661-30-4.mol

Synonyms:

Chemical Property of benzyl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

There total 15 articles about benzyl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 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:

benzyl 2,3-di-O-benzyl-4,6-ol-β-D-galactopyranoside (74801-06-2) → benzyl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside (93661-30-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 81 percent / tetrabutylammonium hydrogensulfate, 5 percent sodium hydroxide / CH₂Cl₂ / 10 h / Heating

2: 87 percent / mercuric cyanide / benzene; nitromethane / 16 h / 45 °C

3: 92 percent / M sodium methoxide / methanol / 5 h / Ambient temperature

4: 91 percent / M sodium methoxide / methanol / 0.67 h / Heating

5: 88 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 2 h / Ambient temperature

6: 82 percent / silver triflate, 2,4,6-trimethylpyridine, molecular sieve 4A / toluene / 1 h / -20 °C

7: 95 percent / M sodium methoxide / methanol / 3 h / Ambient temperature

8: 92 percent / 60 percent acetic acid / 5.5 h / 90 °C

9: 1.) tris(triphenylphosphine)rhodium(I) chloride, 2.) M hydrochloric acid / 1.) ethanol/toluene/water, 20 h, reflux, 2.) acetone, 10 min, reflux

With 2,4,6-trimethyl-pyridine; hydrogenchloride; sodium hydroxide; Wilkinson's catalyst; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; tetra(n-butyl)ammonium hydrogensulfate; mercury(II) cyanide; toluene-4-sulfonic acid; acetic acid; In methanol; nitromethane; dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1016/0008-6215(84)85204-0

Reference yield:

Benzyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside (57783-81-0) → benzyl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside (93661-30-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / mercuric cyanide / benzene; nitromethane / 16 h / 45 °C

2: 92 percent / M sodium methoxide / methanol / 5 h / Ambient temperature

3: 91 percent / M sodium methoxide / methanol / 0.67 h / Heating

4: 88 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 2 h / Ambient temperature

5: 82 percent / silver triflate, 2,4,6-trimethylpyridine, molecular sieve 4A / toluene / 1 h / -20 °C

6: 95 percent / M sodium methoxide / methanol / 3 h / Ambient temperature

7: 92 percent / 60 percent acetic acid / 5.5 h / 90 °C

8: 1.) tris(triphenylphosphine)rhodium(I) chloride, 2.) M hydrochloric acid / 1.) ethanol/toluene/water, 20 h, reflux, 2.) acetone, 10 min, reflux

With 2,4,6-trimethyl-pyridine; hydrogenchloride; Wilkinson's catalyst; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; mercury(II) cyanide; toluene-4-sulfonic acid; acetic acid; In methanol; nitromethane; toluene; acetonitrile; benzene;

DOI:10.1016/0008-6215(84)85204-0

Reference yield:

(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole (20316-77-2) → benzyl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside (93661-30-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 87 percent / Amberlite IR-120(H+) resin / H₂O / 7 h / 60 °C

2: 84 percent / sodium acetate / 0.42 h / Heating

3: 88 percent / hydrogen bromide / CH₂Cl₂; acetic acid / 0.5 h / 0 °C

4: 87 percent / mercuric cyanide / benzene; nitromethane / 16 h / 45 °C

5: 92 percent / M sodium methoxide / methanol / 5 h / Ambient temperature

6: 91 percent / M sodium methoxide / methanol / 0.67 h / Heating

7: 88 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 2 h / Ambient temperature

8: 82 percent / silver triflate, 2,4,6-trimethylpyridine, molecular sieve 4A / toluene / 1 h / -20 °C

9: 95 percent / M sodium methoxide / methanol / 3 h / Ambient temperature

10: 92 percent / 60 percent acetic acid / 5.5 h / 90 °C

11: 1.) tris(triphenylphosphine)rhodium(I) chloride, 2.) M hydrochloric acid / 1.) ethanol/toluene/water, 20 h, reflux, 2.) acetone, 10 min, reflux

With 2,4,6-trimethyl-pyridine; hydrogenchloride; Wilkinson's catalyst; 4 A molecular sieve; Amberlite IR-120(H+) resin; hydrogen bromide; sodium methylate; sodium acetate; silver trifluoromethanesulfonate; mercury(II) cyanide; toluene-4-sulfonic acid; acetic acid; In methanol; nitromethane; dichloromethane; water; acetic acid; toluene; acetonitrile; benzene;

DOI:10.1016/0008-6215(84)85204-0

upstream raw materials:

benzyl O-β-D-glucopyranosyl-(1->2)-O-(3-O-allyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

benzyl 2,3-di-O-benzyl-4,6-ol-β-D-galactopyranoside

Benzyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside

(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole