(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{(2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3,5-dihydroxy-tetrahydro-pyran-4-yloxy}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{(2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3,5-dihydroxy-tetrahydro-pyran-4-yloxy}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 246865-86-1
• Molecular Formula: C₄₁H₆₃NO₁₈Si
• Molecular Weight: 886.033

Synonyms:(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{(2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3,5-dihydroxy-tetrahydro-pyran-4-yloxy}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{(2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3,5-dihydroxy-tetrahydro-pyran-4-yloxy}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{(2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3,5-dihydroxy-tetrahydro-pyran-4-yloxy}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 7 articles about (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{(2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3,5-dihydroxy-tetrahydro-pyran-4-yloxy}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic 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:

5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-(methoxycarbonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl diethyl phosphite (145240-79-5) + Thexyldimethylsilyl 6-O-benzyl-β-D-galactopyranoside (246865-83-8) → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{(2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3,5-dihydroxy-tetrahydro-pyran-4-yloxy}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (246865-86-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -40 ℃; for 0.75h;

DOI:10.1002/(SICI)1521-3765(20000103)6:1<111::AID-CHEM111>3.0.CO;2-X

Reference yield:

2,3,4-tri-O-acetyl-6-O-benzyl-α/β-D-galactopyranose → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{(2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3,5-dihydroxy-tetrahydro-pyran-4-yloxy}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (246865-86-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / imidazole / dimethylformamide / 20 °C

2: 96 percent / NaOMe / methanol / -15 °C

3: TMSOTf / acetonitrile / 0.75 h / -40 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; sodium methylate; In methanol; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Deacetylation / 3: Glycosylation;

DOI:10.1002/(SICI)1521-3765(20000103)6:1<111::AID-CHEM111>3.0.CO;2-X

Reference yield:

methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate (144240-36-8) + Thexyldimethylsilyl 6-O-benzyl-β-D-galactopyranoside (246865-83-8) → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{(2R,3S,4S,5R,6S)-2-benzyloxymethyl-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3,5-dihydroxy-tetrahydro-pyran-4-yloxy}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (246865-86-1)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; MS 3 Angstroem; In acetonitrile; at -40 ℃;

DOI:10.1016/S0040-4039(99)01361-1

upstream raw materials:

methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate

Thexyldimethylsilyl 6-O-benzyl-β-D-galactopyranoside

5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-(methoxycarbonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl diethyl phosphite

chlorodimethyl(1,1,2-trimethylpropyl)silane

Downstream raw materials:

Thexyldimethylsilyl O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-benzyl-β-D-galactopyranoside

(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3S,4S,5R,6S)-3,5-diacetoxy-2-benzyloxymethyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

O-(Methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-benzyl-β-D-galactopyranose

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