ethyl 3,3-diacetamido-4-O-acetyl-2-O-benzyl-1-thio-α-D-fucopyranoside

Base Information

• Chemical Name: ethyl 3,3-diacetamido-4-O-acetyl-2-O-benzyl-1-thio-α-D-fucopyranoside
• CAS No.: 868381-85-5
• Molecular Formula: C₂₁H₂₉NO₆S
• Molecular Weight: 423.53
• Mol file: 868381-85-5.mol

Synonyms:ethyl 3,3-diacetamido-4-O-acetyl-2-O-benzyl-1-thio-α-D-fucopyranoside

Chemical Property of ethyl 3,3-diacetamido-4-O-acetyl-2-O-benzyl-1-thio-α-D-fucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3,3-diacetamido-4-O-acetyl-2-O-benzyl-1-thio-α-D-fucopyranoside

There total 3 articles about ethyl 3,3-diacetamido-4-O-acetyl-2-O-benzyl-1-thio-α-D-fucopyranoside 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: 47.0%

ethyl 3-acetamido-4-O-acetyl-2-O-benzyl-1-thio-D-fucopyranoside (868381-83-3) + acetyl chloride (75-36-5) → ethyl 3,3-diacetamido-4-O-acetyl-2-O-benzyl-1-thio-β-D-fucopyranoside (868381-87-7) + ethyl 3,3-diacetamido-4-O-acetyl-2-O-benzyl-1-thio-α-D-fucopyranoside (868381-85-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jo051153d

Reference yield:

Acetic acid (3R,4S,5R,6R)-5-acetoxy-4-acetylamino-3-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester → ethyl 3,3-diacetamido-4-O-acetyl-2-O-benzyl-1-thio-α-D-fucopyranoside (868381-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 mg / BF₃*Et₂O / CH₂Cl₂ / 20 °C

2: 44 percent / (i-Pr)2NEt / CH₂Cl₂ / 20 °C

With boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo051153d

Reference yield:

4-O-acetyl-3-acetamido-2-O-benzyl-3-deoxy-D-fucopyranose → ethyl 3,3-diacetamido-4-O-acetyl-2-O-benzyl-1-thio-α-D-fucopyranoside (868381-85-5)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 20 °C

2: 90 mg / BF₃*Et₂O / CH₂Cl₂ / 20 °C

3: 44 percent / (i-Pr)2NEt / CH₂Cl₂ / 20 °C

With pyridine; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo051153d

upstream raw materials:

ethyl 3-acetamido-4-O-acetyl-2-O-benzyl-1-thio-D-fucopyranoside

acetyl chloride

Downstream raw materials:

methyl (3,3-diacetamido-4-O-acetyl-2-O-benzyl-α-D-fucopyranosyl)-(1->2)-(3-O-allyl-4-O-benzyl-β-D-rhamnopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-rhamnopyranoside