Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 502692-45-7
• Molecular Formula: C₄₄H₅₀Cl₃NO₁₅S
• Molecular Weight: 971.304

Synonyms:Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

There total 10 articles about Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-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: 70.0%

p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside (502692-44-6) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (502692-45-7)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; toluene; at -10 ℃; for 2.5h;

DOI:10.1021/jo0206420

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (502692-45-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 0.41 g / (+/-)-10-camphorsulfonic acid / acetonitrile / 12 h / 20 °C

2: 82 percent / NaH; Bu₄NI / dimethylformamide / 0 - 20 °C

3: 90 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

4: 80 percent / 1,3-dithiopropane; TEA / methanol; CH₂Cl₂ / 40 °C

5: 90 percent / NaHCO₃ / tetrahydrofuran / 4 h / 20 °C

6: 70 percent / 2,6-di-tert-butyl-4-methylpyridine; molecular sieves (4 Angstroem); silver triflate / CH₂Cl₂; toluene / 2.5 h / -10 °C

With 1.3-propanedithiol; triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; TEA; camphor-10-sulfonic acid; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo0206420

Reference yield:

p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethyloxycarbonylamino)-β-D-glucopyranoside (220645-20-5) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (502692-45-7)

Guidance literature:

Multi-step reaction with 9 steps

1: zinc; AcOH / methanol; CH₂Cl₂ / 1 h / 20 °C

2: NaOMe; MeOH / CH₂Cl₂ / 2 h / 20 °C

3: K₂CO₃; ZnCl₂; triflyl azide / CH₂Cl₂; methanol; H₂O / 18 h / 20 °C

4: 0.41 g / (+/-)-10-camphorsulfonic acid / acetonitrile / 12 h / 20 °C

5: 82 percent / NaH; Bu₄NI / dimethylformamide / 0 - 20 °C

6: 90 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

7: 80 percent / 1,3-dithiopropane; TEA / methanol; CH₂Cl₂ / 40 °C

8: 90 percent / NaHCO₃ / tetrahydrofuran / 4 h / 20 °C

9: 70 percent / 2,6-di-tert-butyl-4-methylpyridine; molecular sieves (4 Angstroem); silver triflate / CH₂Cl₂; toluene / 2.5 h / -10 °C

With 1.3-propanedithiol; methanol; triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; TEA; triflic azide; camphor-10-sulfonic acid; sodium methylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; trifluoroacetic acid; zinc(II) chloride; zinc; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 2: Zemplen deacetylation;

DOI:10.1021/jo0206420

upstream raw materials:

p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

benzaldehyde dimethyl acetal

p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethyloxycarbonylamino)-β-D-glucopyranoside

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