benzyl (3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-O-benzyl-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl (3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-O-benzyl-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside
• CAS No.: 756496-96-5
• Molecular Formula: C₄₄H₆₀O₁₁Si
• Molecular Weight: 793.039

Synonyms:benzyl (3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-O-benzyl-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside

Chemical Property of benzyl (3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-O-benzyl-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-O-benzyl-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside

There total 8 articles about benzyl (3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-O-benzyl-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside 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: 88.0%

benzyl bromide (100-39-0) + benzyl (3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside (756496-95-4) → benzyl (3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-O-benzyl-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside (756496-96-5)

Guidance literature:

benzyl (3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside; With di(n-butyl)tin oxide; In methanol; at 60 ℃; for 15h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In toluene; at 60 ℃; for 17h;

DOI:10.1002/ejoc.200300807

Reference yield:

(2S,3R,4S,5R,6R)-2-((3aR,5R,6S,7S,7aR)-7-Hydroxy-5-hydroxymethyl-2-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol → benzyl (3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-O-benzyl-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside (756496-96-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Bu₂SnO / methanol / 15 h / 60 °C

1.2: 11.84 g / Bu₄NI / toluene / 17 h / 60 °C

2.1: 70 percent / 3 Angstroem molecular sieves; trifluoromethanesulfonic acid / acetonitrile / 0 °C

3.1: camphorsulfonic acid / acetonitrile / 0.5 h

4.1: 1.34 g / collidine / dimethylformamide / 20 °C

5.1: NaOH / ethanol / 40 °C

6.1: nBU₄NF / tetrahydrofuran / -30 - 20 °C

7.1: 176 mg / imidazole / dimethylformamide / 4 h

8.1: Bu₂SnO / methanol / 15 h / 60 °C

8.2: 88 percent / nBu₄NI / toluene / 17 h / 60 °C

With 1H-imidazole; 2,3,5-trimethyl-pyridine; sodium hydroxide; trifluorormethanesulfonic acid; 3 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; di(n-butyl)tin oxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.200300807

Reference yield:

(3-O-allyl-β-D-galactopyranosyl)-(1->4)-[1,2-O-(1-(β-methoxyethylidene)]-α-D-glucopyranose (756496-84-1) → benzyl (3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-O-benzyl-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside (756496-96-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 70 percent / 3 Angstroem molecular sieves; trifluoromethanesulfonic acid / acetonitrile / 0 °C

2.1: camphorsulfonic acid / acetonitrile / 0.5 h

3.1: 1.34 g / collidine / dimethylformamide / 20 °C

4.1: NaOH / ethanol / 40 °C

5.1: nBU₄NF / tetrahydrofuran / -30 - 20 °C

6.1: 176 mg / imidazole / dimethylformamide / 4 h

7.1: Bu₂SnO / methanol / 15 h / 60 °C

7.2: 88 percent / nBu₄NI / toluene / 17 h / 60 °C

With 1H-imidazole; 2,3,5-trimethyl-pyridine; sodium hydroxide; trifluorormethanesulfonic acid; 3 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; di(n-butyl)tin oxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.200300807

upstream raw materials:

benzyl bromide

benzyl (3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside

(3-O-allyl-β-D-galactopyranosyl)-(1->4)-[1,2-O-(1-(β-methoxyethylidene)]-α-D-glucopyranose

Acetic acid (3R,4S,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester

Downstream raw materials:

benzyl (3-O-allyl-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-O-benzyl-6-O-(thexyldimethylsilyl)-α-D-glucopyranoside

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