phenyl (3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-[4,6-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: phenyl (3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-[4,6-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 204199-48-4
• Molecular Formula: C₆₆H₇₀Cl₃NO₁₈S
• Molecular Weight: 1303.7

Synonyms:phenyl (3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-[4,6-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property of phenyl (3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-[4,6-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of phenyl (3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-[4,6-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

There total 20 articles about phenyl (3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-[4,6-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside 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:

C74H78Cl3NO19S → phenyl (3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-[4,6-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (204199-48-4)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In chloroform; at 23 ℃; for 3h;

DOI:10.1021/jo980660a

Reference yield:

benzyl bromide (100-39-0) → phenyl (3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-[4,6-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (204199-48-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: NaH / dimethylformamide / 2 h / 0 °C

2.1: 63.5 g / aq. AcOH / 3 h / 90 °C

3.1: 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 23 °C

3.2: 92 percent / aq. AcOH / 0.17 h

4.1: 63.5 percent / 2,6-di-tert-butyl-4-methylpyridine; 4-Angstroem molecular sieves; silver trifluoromethanesulfonate / CH₂Cl₂ / 2 h / -20 - 0 °C

5.1: 79 percent / HBF₄ / methanol; diethyl ether / 72 h / 23 °C

6.1: 10-camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 23 °C

7.1: 32 g / C₅H₅N / CH₂Cl₂ / 0.17 h / 0 °C

8.1: HBF₄ / methanol; CH₂Cl₂; diethyl ether / 0.5 h / 0 - 23 °C

9.1: C₅H₅N; 4-(dimethylamino)pyridine / 1 h / 0 - 23 °C

10.1: 19.7 g / thiourea / dimethylformamide; pyridine / 0.5 h / 23 °C

11.1: 2,6-di-tert-butyl-4-methylpyridine; 4-Angstroem molecular sieves; methyl trifluoromethanesulfonate / diethyl ether / 66 h / 23 °C

12.1: PPh₃ / CH₂Cl₂ / 48 h / 35 - 40 °C

12.2: 7.9 g / H₂O / CH₂Cl₂ / 24 h / 35 - 40 °C

13.1: NaHCO₃ / acetone; H₂O / 0.05 h / 0 °C

14.1: 6.66 g / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CHCl₃ / 3 h / 23 °C

With pyridine; dmap; tetrafluoroboric acid; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; silver trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; acetic acid; thiourea; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl trifluoromethanesulfonate; In pyridine; methanol; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Esterification / 3.2: Hydrolysis / 4.1: Condensation / 5.1: Deacetylation / 6.1: Cyclization / 7.1: Acylation / 8.1: methanolysis / 9.1: Acetylation / 10.1: dechloroacetylation / 11.1: Condensation / 12.1: Staudinger reaction / 12.2: Hydrolysis / 13.1: Acylation / 14.1: deprotection;

DOI:10.1021/jo980660a

Reference yield:

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (131087-35-9) → phenyl (3,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-[4,6-di-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl]-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (204199-48-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: NaH / dimethylformamide / 2 h / 0 °C

2.1: 63.5 g / aq. AcOH / 3 h / 90 °C

3.1: 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 23 °C

3.2: 92 percent / aq. AcOH / 0.17 h

4.1: 63.5 percent / 2,6-di-tert-butyl-4-methylpyridine; 4-Angstroem molecular sieves; silver trifluoromethanesulfonate / CH₂Cl₂ / 2 h / -20 - 0 °C

5.1: 79 percent / HBF₄ / methanol; diethyl ether / 72 h / 23 °C

6.1: 10-camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 23 °C

7.1: 32 g / C₅H₅N / CH₂Cl₂ / 0.17 h / 0 °C

8.1: HBF₄ / methanol; CH₂Cl₂; diethyl ether / 0.5 h / 0 - 23 °C

9.1: C₅H₅N; 4-(dimethylamino)pyridine / 1 h / 0 - 23 °C

10.1: 19.7 g / thiourea / dimethylformamide; pyridine / 0.5 h / 23 °C

11.1: 2,6-di-tert-butyl-4-methylpyridine; 4-Angstroem molecular sieves; methyl trifluoromethanesulfonate / diethyl ether / 66 h / 23 °C

12.1: PPh₃ / CH₂Cl₂ / 48 h / 35 - 40 °C

12.2: 7.9 g / H₂O / CH₂Cl₂ / 24 h / 35 - 40 °C

13.1: NaHCO₃ / acetone; H₂O / 0.05 h / 0 °C

14.1: 6.66 g / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CHCl₃ / 3 h / 23 °C

With pyridine; dmap; tetrafluoroboric acid; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; silver trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; acetic acid; thiourea; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl trifluoromethanesulfonate; In pyridine; methanol; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Esterification / 3.2: Hydrolysis / 4.1: Condensation / 5.1: Deacetylation / 6.1: Cyclization / 7.1: Acylation / 8.1: methanolysis / 9.1: Acetylation / 10.1: dechloroacetylation / 11.1: Condensation / 12.1: Staudinger reaction / 12.2: Hydrolysis / 13.1: Acylation / 14.1: deprotection;

DOI:10.1021/jo980660a

upstream raw materials:

benzyl bromide

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranose

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

phenyl 4-O-benzyl-1-thio-α-L-rhamnopyranoside

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