Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-(4-methoxy-benzyloxymethyl)-2-phenylsulfanyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-(4-methoxy-benzyloxymethyl)-2-phenylsulfanyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 467447-18-3
• Molecular Formula: C₃₈H₄₇NO₁₆S
• Molecular Weight: 805.854

Synonyms:

Chemical Property of Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-(4-methoxy-benzyloxymethyl)-2-phenylsulfanyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-(4-methoxy-benzyloxymethyl)-2-phenylsulfanyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

There total 5 articles about Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-(4-methoxy-benzyloxymethyl)-2-phenylsulfanyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 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:

acetic anhydride (108-24-7) + phenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside (467447-14-9) → Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-(4-methoxy-benzyloxymethyl)-2-phenylsulfanyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (467447-18-3)

Guidance literature:

phenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside; With ethylenediamine; In ethanol; isopropyl alcohol; at 60 ℃; for 4h;

acetic anhydride; With pyridine; at 20 ℃; for 48h;

DOI:10.1016/S0008-6215(02)00104-0

Reference yield:

phenyl 2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside → Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-(4-methoxy-benzyloxymethyl)-2-phenylsulfanyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (467447-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: (Bu₃Sn)2O / benzene / 16 h / Heating

1.2: 38 percent / Bu₄NI / 18 h / 95 °C

2.1: 59 percent / BF₃*OEt₂ / CH₂Cl₂; hexane / 1.5 h / -30 °C

3.1: 84 percent / pyridine / 16 h / 20 °C

4.1: 1,2-diaminoethane / ethanol; propan-2-ol / 4 h / 60 °C

4.2: 530 mg / pyridine / 48 h / 20 °C

With pyridine; boron trifluoride diethyl etherate; ethylenediamine; bis(tri-n-butyltin)oxide; In ethanol; hexane; dichloromethane; isopropyl alcohol; benzene;

DOI:10.1016/S0008-6215(02)00104-0

Reference yield:

phenyl 2-deoxy-6-O-(4-methoxybenzyl)-2-tetrachlorophthalmido-1-thio-β-D-glucopyranoside (467447-08-1) → Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-(4-methoxy-benzyloxymethyl)-2-phenylsulfanyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (467447-18-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 59 percent / BF₃*OEt₂ / CH₂Cl₂; hexane / 1.5 h / -30 °C

2.1: 84 percent / pyridine / 16 h / 20 °C

3.1: 1,2-diaminoethane / ethanol; propan-2-ol / 4 h / 60 °C

3.2: 530 mg / pyridine / 48 h / 20 °C

With pyridine; boron trifluoride diethyl etherate; ethylenediamine; In ethanol; hexane; dichloromethane; isopropyl alcohol;

DOI:10.1016/S0008-6215(02)00104-0

upstream raw materials:

acetic anhydride

phenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside

phenyl 2-deoxy-6-O-(4-methoxybenzyl)-2-tetrachlorophthalmido-1-thio-β-D-glucopyranoside

phenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-deoxy-6-O-(4-methoxybenzyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

phenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3-O-acetyl-6-O-tert-butyldimethylsilyl-2-deoxy-1-thio-β-D-glucopyranoside

4-nitrophenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3-O-acetyl-2-deoxy-β-D-glucopyranoside

4-nitrophenyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside

phenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside

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