ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside
• CAS No.: 286845-80-5
• Molecular Formula: C₅₀H₆₅NO₂₂S
• Molecular Weight: 1064.13

Synonyms:ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside

Chemical Property of ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside

Chemical Property:

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Technology Process of ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside

There total 13 articles about ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside 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: 73.0%

ethanethiol (75-08-1) + (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-1,2,4,6-tetra-O-acetyl-β-D-galactopyranose (286845-79-2) → ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside (286845-80-5)

Guidance literature:

With molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -10 - 10 ℃; for 2h;

DOI:10.1016/S0957-4166(99)00554-6

Reference yield:

2-(trimethylsilyl)ethyl β-D-galactopyranoside (117252-95-6) → ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside (286845-80-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: p-toluenesulfonic acid / 2 h / pH 1

2.1: pyridine / 0.75 h

3.1: 95 percent / aq. HOAc / 0.67 h / 90 °C

4.1: p-toluenesulfonic acid / acetonitrile / 0.5 h / pH 1

4.2: 79 percent / aq. TFA / acetonitrile / 0.5 h

5.1: 70 percent / molecular sieves; NIS; TfOH / CH₂Cl₂; diethyl ether / 0.33 h / 0 °C

6.1: NaOMe / methanol / 2 h / pH 11

7.1: hydrazine monohydrate / ethanol; dioxane / 1 h / Heating

8.1: pyridine; 4-dimethylaminopyridine / 0.5 h / 0 °C

9.1: 42 percent / BF₃*Et₂O / toluene / 3 h / 20 - 40 °C

10.1: 73 percent / molecular sieves; BF₃*Et₂O / CH₂Cl₂ / 2 h / -10 - 10 °C

With pyridine; dmap; N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; In 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; toluene; acetonitrile; 1.1: acetalization / 2.1: Acylation / 3.1: deacetalization / 4.1: Acylation / 4.2: Hydrolysis / 5.1: Condensation / 6.1: deprotection / 7.1: deprotection / 8.1: Acetylation / 9.1: Acetylation / 10.1: thioalkylation;

DOI:10.1016/S0957-4166(99)00554-6

Reference yield:

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (115533-35-2) → ethyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside (286845-80-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / molecular sieves 4A; AgOTf / toluene; CH₂Cl₂ / 0.5 h / -45 °C

2: 70 percent / molecular sieves; NIS; TfOH / CH₂Cl₂; diethyl ether / 0.33 h / 0 °C

3: NaOMe / methanol / 2 h / pH 11

4: hydrazine monohydrate / ethanol; dioxane / 1 h / Heating

5: pyridine; 4-dimethylaminopyridine / 0.5 h / 0 °C

6: 42 percent / BF₃*Et₂O / toluene / 3 h / 20 - 40 °C

7: 73 percent / molecular sieves; BF₃*Et₂O / CH₂Cl₂ / 2 h / -10 - 10 °C

With pyridine; dmap; N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; hydrazine hydrate; In 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; toluene; 1: Condensation / 2: Condensation / 3: deprotection / 4: deprotection / 5: Acetylation / 6: Acetylation / 7: thioalkylation;

DOI:10.1016/S0957-4166(99)00554-6

upstream raw materials:

ethanethiol

(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-1,2,4,6-tetra-O-acetyl-β-D-galactopyranose

2-(trimethylsilyl)ethyl β-D-galactopyranoside

ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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