benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-2-O-acetyl-3,6-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside

Base Information

Chemical Name:benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-2-O-acetyl-3,6-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside
CAS No.:756496-86-3
Molecular Formula:C₄₉H₈₀O₁₂Si₃
Molecular Weight:945.423
Hs Code.:

benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-2-O-acetyl-3,6-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside

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Chemical Property of benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-2-O-acetyl-3,6-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside

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Technology Process of benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-2-O-acetyl-3,6-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside

There total 5 articles about benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-2-O-acetyl-3,6-di-O-(tert-butyldimethylsilyl)-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:

: 69739-34-0
t-butyldimethylsiyl triflate

: Acetic acid (3R,4S,5S,6R)-5-((2S,4aR,6S,7R,8R,8aS)-8-allyloxy-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-benzyloxy-4-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester

: 756496-98-7
benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-2-O-acetyl-3,6-di-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside

: 756496-86-3
benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-2-O-acetyl-3,6-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside

Guidance literature:: With 2,3,5-trimethyl-pyridine; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1002/ejoc.200300807

Reference yield:

: 299174-87-1
2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

: 756496-86-3
benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-2-O-acetyl-3,6-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaOMe; MeOH / 4 h

2.1: Bu₂SnO / methanol / 15 h / 60 °C

2.2: 11.84 g / Bu₄NI / toluene / 17 h / 60 °C

3.1: 70 percent / 3 Angstroem molecular sieves; trifluoromethanesulfonic acid / acetonitrile / 0 °C

4.1: camphorsulfonic acid / acetonitrile / 0.5 h

5.1: 1.34 g / collidine / dimethylformamide / 20 °C

With 2,3,5-trimethyl-pyridine; methanol; trifluorormethanesulfonic acid; 3 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; di(n-butyl)tin oxide; In methanol; N,N-dimethyl-formamide; acetonitrile; 1.1: Zemplen deacetylation;
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

: 756496-86-3
benzyl [3-O-allyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-(1->4)-2-O-acetyl-3,6-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 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

With 2,3,5-trimethyl-pyridine; trifluorormethanesulfonic acid; 3 A molecular sieve; camphor-10-sulfonic acid; di(n-butyl)tin oxide; In methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.200300807