Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(R)-2-(dimethyl-phenyl-silanyl)-1-((2S,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(R)-2-(dimethyl-phenyl-silanyl)-1-((2S,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 122588-58-3
• Molecular Formula: C₅₁H₆₂O₁₅Si
• Molecular Weight: 943.13

Synonyms:

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(R)-2-(dimethyl-phenyl-silanyl)-1-((2S,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(R)-2-(dimethyl-phenyl-silanyl)-1-((2S,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-tetrahydro-pyran-3-yl ester

There total 3 articles about Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(R)-2-(dimethyl-phenyl-silanyl)-1-((2S,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-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: 60.0%

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3) + methyl-2,3,4-tri-O-benzyl-7-(Si-dimethylphenyl-silyl)-L-glycero-α-Dmanno-heptopyranoside (122588-55-0) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(R)-2-(dimethyl-phenyl-silanyl)-1-((2S,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-tetrahydro-pyran-3-yl ester (122588-58-3)

Guidance literature:

With mercury(II) cyanide; mercury dibromide; In acetonitrile;

DOI:10.1016/S0040-4039(00)95167-0

Reference yield:

methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside (40653-15-4) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(R)-2-(dimethyl-phenyl-silanyl)-1-((2S,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-tetrahydro-pyran-3-yl ester (122588-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / tetrahydrofuran / 1.5 h / 0 °C

2: 60 percent / Hg(CN)2/HgBr₂ / acetonitrile

With mercury(II) cyanide; mercury dibromide; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4039(00)95167-0

Reference yield:

[(dimethylphenylsilyl)methyl]magnesium chloride (107735-20-6) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(R)-2-(dimethyl-phenyl-silanyl)-1-((2S,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-tetrahydro-pyran-3-yl ester (122588-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / tetrahydrofuran / 1.5 h / 0 °C

2: 60 percent / Hg(CN)2/HgBr₂ / acetonitrile

With mercury(II) cyanide; mercury dibromide; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4039(00)95167-0

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

methyl-2,3,4-tri-O-benzyl-7-(Si-dimethylphenyl-silyl)-L-glycero-α-Dmanno-heptopyranoside

methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside

[(dimethylphenylsilyl)methyl]magnesium chloride

Downstream raw materials:

Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(S)-2-hydroxy-1-((2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethoxy]-tetrahydro-pyran-3-yl ester

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