9-[(2R,3R,4R,5S,6R)-3-Acetylamino-4-allyloxy-6-benzyloxymethyl-5-((2S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

Base Information

• Chemical Name: 9-[(2R,3R,4R,5S,6R)-3-Acetylamino-4-allyloxy-6-benzyloxymethyl-5-((2S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester
• CAS No.: 98807-84-2
• Molecular Formula: C₅₅H₇₁NO₁₂
• Molecular Weight: 938.168

Synonyms:9-[(2R,3R,4R,5S,6R)-3-Acetylamino-4-allyloxy-6-benzyloxymethyl-5-((2S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

Chemical Property of 9-[(2R,3R,4R,5S,6R)-3-Acetylamino-4-allyloxy-6-benzyloxymethyl-5-((2S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

Chemical Property:

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Technology Process of 9-[(2R,3R,4R,5S,6R)-3-Acetylamino-4-allyloxy-6-benzyloxymethyl-5-((2S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

There total 6 articles about 9-[(2R,3R,4R,5S,6R)-3-Acetylamino-4-allyloxy-6-benzyloxymethyl-5-((2S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl 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: 57.0%

8-methoxycarbonyloctyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-2-O-phenoxythiocarbonyl-β-D-galactopyranosyl)-β-D-glucopyranoside (98807-83-1) → 9-[(2R,3R,4R,5S,6R)-3-Acetylamino-4-allyloxy-6-benzyloxymethyl-5-((2S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (98807-84-2)

Guidance literature:

With azobisisobutyronitrile; tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 2h;

DOI:10.1016/0008-6215(85)85204-6

Reference yield:

8-methoxycarbonyloctyl 2-acetamido-3-O-allyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (98856-38-3) → 9-[(2R,3R,4R,5S,6R)-3-Acetylamino-4-allyloxy-6-benzyloxymethyl-5-((2S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (98807-84-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / NaBH₃CN, HCl, molecular sieve 3 Angstroem / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

2: 88 percent / Hg(CN)2, molecular sieve 4 Angstroem / benzene; nitromethane / 16 h / Ambient temperature

3: 85 percent / 0.01 M MeONa / methanol / 144 h / Ambient temperature

4: 79 percent / 4-dimethylaminopyridine / acetonitrile / reflux 5 h, then RT 16 h

5: 57 percent / α,α'-azobisisobutyronitrile, tributylstannane / toluene / 2 h / 80 °C

With hydrogenchloride; dmap; 3 A molecular sieve; 4 A molecular sieve; azobisisobutyronitrile; tri-n-butyl-tin hydride; sodium methylate; mercury(II) cyanide; sodium cyanoborohydride; In tetrahydrofuran; methanol; diethyl ether; nitromethane; toluene; acetonitrile; benzene;

DOI:10.1016/0008-6215(85)85204-6

Reference yield:

2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl bromide (84439-23-6) → 9-[(2R,3R,4R,5S,6R)-3-Acetylamino-4-allyloxy-6-benzyloxymethyl-5-((2S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (98807-84-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / Hg(CN)2, molecular sieve 4 Angstroem / benzene; nitromethane / 16 h / Ambient temperature

2: 85 percent / 0.01 M MeONa / methanol / 144 h / Ambient temperature

3: 79 percent / 4-dimethylaminopyridine / acetonitrile / reflux 5 h, then RT 16 h

4: 57 percent / α,α'-azobisisobutyronitrile, tributylstannane / toluene / 2 h / 80 °C

With dmap; 4 A molecular sieve; azobisisobutyronitrile; tri-n-butyl-tin hydride; sodium methylate; mercury(II) cyanide; In methanol; nitromethane; toluene; acetonitrile; benzene;

DOI:10.1016/0008-6215(85)85204-6

upstream raw materials:

8-methoxycarbonyloctyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-2-O-phenoxythiocarbonyl-β-D-galactopyranosyl)-β-D-glucopyranoside

2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl bromide

8-methoxycarbonyloctyl 2-acetamido-3-O-allyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

8-methoxycarbonyloctyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

8-methoxycarbonyloctyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside

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