Chloro-acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Chloro-acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester
• CAS No.: 152932-85-9
• Molecular Formula: C₄₁H₄₂ClNO₁₅S
• Molecular Weight: 856.301

Synonyms:Chloro-acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester

Chemical Property of Chloro-acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester

Chemical Property:

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Technology Process of Chloro-acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester

There total 2 articles about Chloro-acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-4-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:

Chloro-acetic acid (2R,3S,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-fluoro-tetrahydro-pyran-4-yl ester → Chloro-acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester (152932-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / AgOTf, Cp₂HfCl₂, 2,6-di-tert-butyl-4-methylpyridine, 4A-molecular sieves / CH₂Cl₂ / 6 h / 0 - 25 °C

2: 76 percent / NaCNBH₃, HCl, 3A-molecular sieves / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

With hydrogenchloride; 2,6-di-tert-butyl-4-methylpyridine; bis(cyclopentadienyl)hafnium dichloride; 3 A molecular sieve; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja00072a049

Reference yield:

phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (127061-09-0) → Chloro-acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester (152932-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / AgOTf, Cp₂HfCl₂, 2,6-di-tert-butyl-4-methylpyridine, 4A-molecular sieves / CH₂Cl₂ / 6 h / 0 - 25 °C

2: 76 percent / NaCNBH₃, HCl, 3A-molecular sieves / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

With hydrogenchloride; 2,6-di-tert-butyl-4-methylpyridine; bis(cyclopentadienyl)hafnium dichloride; 3 A molecular sieve; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja00072a049

Reference yield: 95.0%

2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride (127061-08-9) + Chloro-acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-4-yl ester (152932-85-9) → C68H70ClNO19S (152932-86-0)

Guidance literature:

With 4 A molecular sieve; silver perchlorate; tin(ll) chloride; In tetrahydrofuran; diethyl ether; at -10 - 0 ℃; for 1h;

DOI:10.1021/ja00072a049

upstream raw materials:

phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

C₆₈H₇₀ClNO₁₉S

C₅₅H₆₅NO₁₈S

C₆₂H₆₅ClFNO₁₉

C₆₇H₇₁NO₁₉

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