Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 212713-53-6
• Molecular Formula: C₃₈H₅₆Cl₃NO₁₆Si
• Molecular Weight: 917.304

Synonyms:Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

There total 4 articles about Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-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: 87.0%

C38H54Cl3NO16Si (212713-51-4) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (212713-53-6)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; for 2h;

DOI:10.1080/07328309808002349

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (212713-53-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / p-TsOH / acetonitrile / 2 h

2: 93 percent / TMSOTf / CH₂Cl₂ / 0.17 h / Ambient temperature

3: 87 percent / NaCNBH₃, HCl / tetrahydrofuran; diethyl ether / 2 h

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1080/07328309808002349

Reference yield:

{(2S,3R,4R,5S,6R)-2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (212713-53-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / p-TsOH / acetonitrile / 2 h

2: 93 percent / TMSOTf / CH₂Cl₂ / 0.17 h / Ambient temperature

3: 87 percent / NaCNBH₃, HCl / tetrahydrofuran; diethyl ether / 2 h

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1080/07328309808002349

upstream raw materials:

C₃₈H₅₄Cl₃NO₁₆Si

benzaldehyde dimethyl acetal

Downstream raw materials:

thexyldimethylsilyl O-(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->4)-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

C₄₇H₅₈Cl₃NO₂₂

C₄₉H₅₈Cl₆N₂O₂₂

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