Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 188423-98-5
• Molecular Formula: C₃₉H₄₅NO₁₅
• Molecular Weight: 767.784

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester

There total 5 articles about Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-4-methoxy-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: 13.9%

2,4,6-tri-O-acetate-3-O-methyl-α-D-glucopyranosylbromide (30694-94-1) + p-nitrophenyl 2,4-di-O-benzyl-α-L-rhamnopyranoside (188423-94-1) → Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester (188423-98-5) + Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:

With mercury dibromide; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1016/S0008-6215(96)00255-8

Reference yield:

p-nitrophenyl 4-O-benzyl-α-L-rhamnopyranoside (150412-46-7) → Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester (188423-98-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / p-TsOH / 0.25 h / Ambient temperature

2: 78.9 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 0.17 h

3: 44.3 percent / HgBr₂ / CH₂Cl₂ / 48 h / Ambient temperature

With lithium aluminium tetrahydride; aluminium trichloride; toluene-4-sulfonic acid; mercury dibromide; In diethyl ether; dichloromethane;

DOI:10.1016/S0008-6215(96)00255-8

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester (188423-98-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / p-TsOH / 0.25 h / Ambient temperature

2: 78.9 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 0.17 h

3: 44.3 percent / HgBr₂ / CH₂Cl₂ / 48 h / Ambient temperature

With lithium aluminium tetrahydride; aluminium trichloride; toluene-4-sulfonic acid; mercury dibromide; In diethyl ether; dichloromethane;

DOI:10.1016/S0008-6215(96)00255-8

upstream raw materials:

2,4,6-tri-O-acetate-3-O-methyl-α-D-glucopyranosylbromide

p-nitrophenyl 2,4-di-O-benzyl-α-L-rhamnopyranoside

benzaldehyde dimethyl acetal

benzyl bromide

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