phenyl 3-O-(4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-2,6-di-O-benzoyl-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 3-O-(4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-2,6-di-O-benzoyl-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
CAS No.:578738-10-0
Molecular Formula:C₆₀H₆₂O₁₉S
Molecular Weight:1119.21
Hs Code.:

phenyl 3-O-(4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-2,6-di-O-benzoyl-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside

Synonyms:phenyl 3-O-(4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-2,6-di-O-benzoyl-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 3-O-(4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-2,6-di-O-benzoyl-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 3-O-(4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-2,6-di-O-benzoyl-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside

There total 6 articles about phenyl 3-O-(4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-2,6-di-O-benzoyl-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-1-thio-β-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: 79.0%

: 195712-28-8
phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1-4)-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside

: 578738-07-5
phenyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-β-L-rhamnopyranoside

: 578738-10-0
phenyl 3-O-(4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-2,6-di-O-benzoyl-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; MS 4 Angstroem; In chloroform; at -30 ℃; for 0.25h;
DOI:10.1016/S0008-6215(03)00053-3

Reference yield:

: 73-34-7
L-rhamnose

: 578738-10-0
phenyl 3-O-(4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-2,6-di-O-benzoyl-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 20 °C

2: 33 percent HBr(AcOH) / acetic anhydride; CH₂Cl₂ / 4 h / 20 °C

3: KOH / aq. ethanol; acetone / 20 °C

4: NaOMe / methanol / 2 h / 20 °C

5: pTsOH / acetonitrile / 10 h / 20 °C

6: 92 percent / pyridine / 20 °C

7: 79 percent / MS 4 Angstroem; NIS; TfOH / CHCl₃ / 0.25 h / -30 °C

With pyridine; potassium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; MS 4 Angstroem; hydrogen bromide; sodium methylate; toluene-4-sulfonic acid; In methanol; ethanol; dichloromethane; chloroform; acetic anhydride; acetone; acetonitrile;
DOI:10.1016/S0008-6215(03)00053-3

Reference yield:

: 5158-64-5
2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide

: 578738-10-0
phenyl 3-O-(4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl)-2,6-di-O-benzoyl-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: KOH / aq. ethanol; acetone / 20 °C

2: NaOMe / methanol / 2 h / 20 °C

3: pTsOH / acetonitrile / 10 h / 20 °C

4: 92 percent / pyridine / 20 °C

5: 79 percent / MS 4 Angstroem; NIS; TfOH / CHCl₃ / 0.25 h / -30 °C

With pyridine; potassium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; MS 4 Angstroem; sodium methylate; toluene-4-sulfonic acid; In methanol; ethanol; chloroform; acetone; acetonitrile;
DOI:10.1016/S0008-6215(03)00053-3