Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester
• CAS No.: 143571-59-9
• Molecular Formula: C₅₂H₆₁NO₁₅Si
• Molecular Weight: 968.14

Synonyms:Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

There total 1 articles about Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-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: 76.0%

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide (70831-94-6) + 2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside (143571-58-8) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (143571-59-9)

Guidance literature:

With 4 A molecular sieve; silver perchlorate; silver carbonate; In dichloromethane;

DOI:10.1016/S0008-6215(00)90524-X

Reference yield:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (143571-59-9) → N-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide (143571-61-3)

Guidance literature:

Multi-step reaction with 4 steps

1: O-deacetylation

2: N₂H₄*H₂O / aq. ethanol / Heating

3: N-acetylation

4: 88 percent / p-toluenesulfonic acid

With toluene-4-sulfonic acid; hydrazine hydrate; In ethanol;

DOI:10.1016/S0008-6215(00)90524-X

Reference yield:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (143571-59-9) → 2-(trimethylsilyl)ethyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-O-(2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside (143571-63-5)

Guidance literature:

Multi-step reaction with 6 steps

1: O-deacetylation

2: N₂H₄*H₂O / aq. ethanol / Heating

3: N-acetylation

4: 88 percent / p-toluenesulfonic acid

5: 97 percent / dimethyl(methylthio)sulfonium triflate, MS-4A / benzene / 10 h / 5 - 10 °C

6: 77 percent / sodium cyanoborohydride, HCl / tetrahydrofuran

With hydrogenchloride; sodium cyanoborohydride; toluene-4-sulfonic acid; hydrazine hydrate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In tetrahydrofuran; ethanol; benzene;

DOI:10.1016/S0008-6215(00)90524-X

upstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

2-(Trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside

Downstream raw materials:

2-(Trimethylsilyl)ethyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

N-{(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

2-(trimethylsilyl)ethyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-O-(2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside

C₇₄H₈₇NO₁₅Si

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