N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Base Information

Chemical Name:N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
CAS No.:215302-21-9
Molecular Formula:C₄₉H₆₉NO₁₂
Molecular Weight:864.086
Hs Code.:

N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

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Chemical Property of N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

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Technology Process of N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

There total 8 articles about N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 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:

: 111-87-5
octanol

: 215302-21-9
N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: 35 percent / BF₃*Et₂O / acetonitrile / 18 h / Heating

2: 73 percent / p-toluenesulfonic acid / acetonitrile / 3 h / Ambient temperature

3: Bu₄NBr, 4A molecular sieves / dimethylformamide / 18 h / Ambient temperature

4: 74 percent / camphorsulfonic acid / methanol / 1.5 h / 50 °C

5: 1.) NaH / 1.) DMF, RT, 5 min, 2.) DMF, 40 deg C, 8 h

With 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium hydride; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm980365i

Reference yield:

: 7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4
N-Acetyl-D-glucosamine

: 215302-21-9
N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: 35 percent / BF₃*Et₂O / acetonitrile / 18 h / Heating

2: 73 percent / p-toluenesulfonic acid / acetonitrile / 3 h / Ambient temperature

3: Bu₄NBr, 4A molecular sieves / dimethylformamide / 18 h / Ambient temperature

4: 74 percent / camphorsulfonic acid / methanol / 1.5 h / 50 °C

5: 1.) NaH / 1.) DMF, RT, 5 min, 2.) DMF, 40 deg C, 8 h

With 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium hydride; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm980365i

Reference yield:

: 116514-50-2,128962-63-0,131545-02-3,136758-06-0,99409-34-4,116391-11-8
ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

: 215302-21-9
N-[(2S,3R,4R,5S,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxymethyl)-5-hydroxy-2-octyloxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 4 steps

1: Br₂ / CH₂Cl₂ / 0.5 h / 0 °C

2: Bu₄NBr, 4A molecular sieves / dimethylformamide / 18 h / Ambient temperature

3: 74 percent / camphorsulfonic acid / methanol / 1.5 h / 50 °C

4: 1.) NaH / 1.) DMF, RT, 5 min, 2.) DMF, 40 deg C, 8 h

With 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutylammomium bromide; bromine; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm980365i