acetic acid 3-acetoxy-2-acetoxymethyl-6-[4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: acetic acid 3-acetoxy-2-acetoxymethyl-6-[4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester
• CAS No.: 914772-40-0
• Molecular Formula: C₇₀H₇₈Cl₃NO₂₀
• Molecular Weight: 1359.74

Synonyms:acetic acid 3-acetoxy-2-acetoxymethyl-6-[4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester

Chemical Property of acetic acid 3-acetoxy-2-acetoxymethyl-6-[4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester

Chemical Property:

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Technology Process of acetic acid 3-acetoxy-2-acetoxymethyl-6-[4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester

There total 4 articles about acetic acid 3-acetoxy-2-acetoxymethyl-6-[4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-5-(2,2,2-trichloro-ethoxycarbonylamino)-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: 91.0%

methyl 2,3,6-tri-O-benzyl-4-O-(2',3',6'-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside (19474-56-7,19474-57-8,127243-56-5,92733-60-3) + 1-trichloroacetamido-2-deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-α-D-galactopyranose 3,4,6-triacetate (195142-26-8) → acetic acid 3-acetoxy-2-acetoxymethyl-6-[4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester (914772-40-0)

Guidance literature:

methyl 2,3,6-tri-O-benzyl-4-O-(2',3',6'-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside; 1-trichloroacetamido-2-deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-α-D-galactopyranose 3,4,6-triacetate; 4 A molecular sieve; In diethyl ether; at 20 ℃; for 1h;

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at -20 ℃; for 4h;

DOI:10.1016/j.tetlet.2006.08.008

Reference yield:

β-D-galactosamine hydrochloride (14257-79-5) → acetic acid 3-acetoxy-2-acetoxymethyl-6-[4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester (914772-40-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaOMe / methanol / 0.5 h / 20 °C

1.2: Et₃N / 2 h / 20 °C

1.3: pyridine / 20 °C

2.1: hydrazine acetate / dimethylformamide / 2 h / 0 °C

2.2: DBU / CH₂Cl₂ / 5 h / -10 °C

3.1: 4 Angstroem molecular sieves / diethyl ether / 1 h / 20 °C

3.2: 91 percent / TMSOTf / diethyl ether / 4 h / -20 °C

With sodium methylate; hydrazinium monoacetate; 4 A molecular sieve; In methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2006.08.008

Reference yield:

methyl 2,3,6,2',3'-penta-O-benzyl-4',6'-O-benzylidene-β-lactoside (914772-34-2) → acetic acid 3-acetoxy-2-acetoxymethyl-6-[4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yloxy]-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester (914772-40-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / NaCNBH₃; HCl / diethyl ether; tetrahydrofuran / 0.5 h

2.1: 4 Angstroem molecular sieves / diethyl ether / 1 h / 20 °C

2.2: 91 percent / TMSOTf / diethyl ether / 4 h / -20 °C

With hydrogenchloride; sodium cyanoborohydride; 4 A molecular sieve; In tetrahydrofuran; diethyl ether;

DOI:10.1016/j.tetlet.2006.08.008

upstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-O-(2',3',6'-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside

1-trichloroacetamido-2-deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-α-D-galactopyranose 3,4,6-triacetate

β-D-galactosamine hydrochloride

methyl 2,3,6,2',3'-penta-O-benzyl-4',6'-O-benzylidene-β-lactoside

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