allyl 3-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-glucopyranosiduronic acid

Base Information

Chemical Name:allyl 3-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-glucopyranosiduronic acid
CAS No.:150969-36-1
Molecular Formula:C₄₃H₄₆O₁₂
Molecular Weight:754.831
Hs Code.:

Synonyms:

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Chemical Property of allyl 3-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-glucopyranosiduronic acid

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Technology Process of allyl 3-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-glucopyranosiduronic acid

There total 13 articles about allyl 3-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-glucopyranosiduronic acid 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:

: 71925-96-7
allyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

: 150969-36-1
allyl 3-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 1) t-BuOK, 2) HgO, HgCl₂ / 1) DMF, 80 deg C, 2 h, 2) acetone, H₂O, rt, 2 h

2: 96 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 2 h

3: 60 percent / mol sieves 4A, Me₃SiOSO₂CF₃ / CH₂Cl₂; diethyl ether / 16 h / -70 °C

4: 76 percent / 70percent aq. HClO₄ / CH₂Cl₂

5: CrO₃, conc. H₂SO₄ / acetone; H₂O / 5 h / 0 deg C to rt

6: diethyl ether; CH₂Cl₂

7: 1) NaOMe (pH 11), 2) 1 M LiOH / 1) CH₂Cl₂, MeOH, 20 h, 2) acetone, 3 h

With chromium(VI) oxide; lithium hydroxide; perchloric acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; potassium tert-butylate; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dichloride; mercury(II) oxide; In diethyl ether; dichloromethane; water; acetone;
DOI:10.1016/S0040-4020(01)82378-4

Reference yield:

: 143419-08-3
allyl 2-O-acetyl-3-O-benzyl-β-D-glucopyranoside

: 150969-36-1
allyl 3-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / pyridine / 20 h / 90 °C

2: 60 percent / mol sieves 4A, Me₃SiOSO₂CF₃ / CH₂Cl₂; diethyl ether / 16 h / -70 °C

3: 76 percent / 70percent aq. HClO₄ / CH₂Cl₂

4: CrO₃, conc. H₂SO₄ / acetone; H₂O / 5 h / 0 deg C to rt

5: diethyl ether; CH₂Cl₂

6: 1) NaOMe (pH 11), 2) 1 M LiOH / 1) CH₂Cl₂, MeOH, 20 h, 2) acetone, 3 h

With pyridine; chromium(VI) oxide; lithium hydroxide; perchloric acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; sodium methylate; In diethyl ether; dichloromethane; water; acetone;
DOI:10.1016/S0040-4020(01)82378-4

Reference yield:

: 130539-41-2
allyl 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranoside

: 150969-36-1
allyl 3-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 10 steps

1: NaOCH₃ (pH 11 - 12) / CH₂Cl₂; methanol

2: p-TsOH / acetone / 3 h

3: pyridine / 20 h

4: Dowex-50 (H+) / methanol / 2 h / 65 °C

5: 78 percent / pyridine / 20 h / 90 °C

6: 60 percent / mol sieves 4A, Me₃SiOSO₂CF₃ / CH₂Cl₂; diethyl ether / 16 h / -70 °C

7: 76 percent / 70percent aq. HClO₄ / CH₂Cl₂

8: CrO₃, conc. H₂SO₄ / acetone; H₂O / 5 h / 0 deg C to rt

9: diethyl ether; CH₂Cl₂

10: 1) NaOMe (pH 11), 2) 1 M LiOH / 1) CH₂Cl₂, MeOH, 20 h, 2) acetone, 3 h

With pyridine; chromium(VI) oxide; lithium hydroxide; perchloric acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Dowex-50 (H+); sulfuric acid; sodium methylate; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane; water; acetone;
DOI:10.1016/S0040-4020(01)82378-4