2-{3-[5-acetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yloxy}-propionic acid 2-benzenesulfonyl-ethyl ester

Base Information

• Chemical Name: 2-{3-[5-acetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yloxy}-propionic acid 2-benzenesulfonyl-ethyl ester
• CAS No.: 1053650-20-6
• Molecular Formula: C₄₁H₅₁Cl₃N₂O₁₈S
• Molecular Weight: 998.284

Synonyms:

Chemical Property of 2-{3-[5-acetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yloxy}-propionic acid 2-benzenesulfonyl-ethyl ester

Chemical Property:

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Safty Information:

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Useful:

Technology Process of 2-{3-[5-acetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yloxy}-propionic acid 2-benzenesulfonyl-ethyl ester

There total 6 articles about 2-{3-[5-acetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yloxy}-propionic acid 2-benzenesulfonyl-ethyl 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:

2-{3-acetylamino-2-benzyloxy-6-benzyloxymethyl-5-[2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-4-yloxy}-propionic acid 2-benzenesulfonyl-ethyl ester (919078-15-2) + acetic anhydride (108-24-7) → 2-{3-[5-acetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yloxy}-propionic acid 2-benzenesulfonyl-ethyl ester (1053650-20-6)

Guidance literature:

With zinc(II) chloride; In acetic acid; at 20 ℃;

DOI:10.1002/ejoc.200600515

Reference yield:

benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (914642-50-5) → 2-{3-[5-acetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yloxy}-propionic acid 2-benzenesulfonyl-ethyl ester (1053650-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / NIS; TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 21 h / -45 - 20 °C

2: ZnCl₂ / acetic acid / 20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; zinc(II) chloride; In dichloromethane; acetic acid;

DOI:10.1002/ejoc.200600515

Reference yield:

(6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (919078-13-0) → 2-{3-[5-acetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yloxy}-propionic acid 2-benzenesulfonyl-ethyl ester (1053650-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / NIS; TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 21 h / -45 - 20 °C

2: ZnCl₂ / acetic acid / 20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; zinc(II) chloride; In dichloromethane; acetic acid;

DOI:10.1002/ejoc.200600515

upstream raw materials:

2-{3-acetylamino-2-benzyloxy-6-benzyloxymethyl-5-[2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-4-yloxy}-propionic acid 2-benzenesulfonyl-ethyl ester

acetic anhydride

benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

(6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid 2,2,2-trichloro-ethyl ester

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