5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide

Base Information

Chemical Name:5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide
CAS No.:186831-49-2
Molecular Formula:C₂₇H₃₅BrO₁₂
Molecular Weight:631.472
Hs Code.:

Synonyms:5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide

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Chemical Property of 5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide

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Technology Process of 5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide

There total 6 articles about 5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide 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:

: 186831-45-8
Acetic acid (2S,3R,4R,5S)-5-((S)-1-acetoxy-ethyl)-4-benzyloxy-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl ester

: 186831-49-2
5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide

Guidance literature:: With titanium(IV) bromide;

Reference yield:

: 143394-72-3
1,2,3,4-tetra-O-acetyl-6-deoxy-α-L-talopyranose

: 186831-49-2
5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide

Guidance literature:: Multi-step reaction with 4 steps

1: 79.5 percent / Cl₂CHOCH₃ (DCMME), ZnCl₂ / CH₂Cl₂ / Ambient temperature

2: 73 percent / AgOTf, sym.-collidine / CH₂Cl₂ / 0.5 h / -40 °C

3: 71 percent / TfOH / Ambient temperature

4: TiBr₄ / CH₂Cl₂; acetic acid / 1 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; trifluorormethanesulfonic acid; Dichloromethyl methyl ether; silver trifluoromethanesulfonate; titanium(IV) bromide; zinc(II) chloride; In dichloromethane; acetic acid;
DOI:10.1016/S0008-6215(97)10073-8

Reference yield:

: 143332-42-7
2,3,4-O-triacetyl-6-deoxy-α-L-talose

: 186831-49-2
5-O-acetyl-3-O-benzyl-2-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-talopyranosyl)-α-L-rhamnofuranosyl bromide

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / pyridine

2: 79.5 percent / Cl₂CHOCH₃ (DCMME), ZnCl₂ / CH₂Cl₂ / Ambient temperature

3: 73 percent / AgOTf, sym.-collidine / CH₂Cl₂ / 0.5 h / -40 °C

4: 71 percent / TfOH / Ambient temperature

5: TiBr₄ / CH₂Cl₂; acetic acid / 1 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; trifluorormethanesulfonic acid; Dichloromethyl methyl ether; silver trifluoromethanesulfonate; titanium(IV) bromide; zinc(II) chloride; In pyridine; dichloromethane; acetic acid;
DOI:10.1016/S0008-6215(97)10073-8