Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 182865-85-6
• Molecular Formula: C₅₈H₇₁NO₁₉
• Molecular Weight: 1086.2
• Mol file: 182865-85-6.mol

Synonyms:

Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

There total 8 articles about Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-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: 87.0%

acetic anhydride (108-24-7) + Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-amino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (182865-84-5) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (182865-85-6)

Guidance literature:

With pyridine; dmap;

DOI:10.1016/0960-894X(96)00370-8

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose (112929-24-5,112929-25-6) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (182865-85-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / TMSOTf, MS₄A / 1,2-dichloro-ethane

2: 98 percent / NaOMe / methanol

3: 100 percent / p-TosOH / acetonitrile

4: 61 percent / Hg(CN)2, HgBr₂, MS₄A / 1,2-dichloro-ethane

5: 73 percent / NaBH₃CN, TMSCl / tetrahydrofuran / 0 deg C -> room temperature

6: 80 percent / TMSOTf / diethyl ether; tetrahydrofuran

7: 94 percent / Pd(PPh₃)4, polymethylhydrosiloxane / tetrahydrofuran

8: 87 percent / DMAP, pyridine

With pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; polymethylhydrosiloxane; trimethylsilyl trifluoromethanesulfonate; sodium methylate; mercury(II) cyanide; sodium cyanoborohydride; toluene-4-sulfonic acid; mercury dibromide; In tetrahydrofuran; methanol; diethyl ether; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/0960-894X(96)00370-8

Reference yield:

((2R,3R,4R,5S,6R)-2-Ethoxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid allyl ester (182865-98-1) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester (182865-85-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / p-TosOH / acetonitrile

2: 61 percent / Hg(CN)2, HgBr₂, MS₄A / 1,2-dichloro-ethane

3: 73 percent / NaBH₃CN, TMSCl / tetrahydrofuran / 0 deg C -> room temperature

4: 80 percent / TMSOTf / diethyl ether; tetrahydrofuran

5: 94 percent / Pd(PPh₃)4, polymethylhydrosiloxane / tetrahydrofuran

6: 87 percent / DMAP, pyridine

With pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; polymethylhydrosiloxane; trimethylsilyl trifluoromethanesulfonate; mercury(II) cyanide; sodium cyanoborohydride; toluene-4-sulfonic acid; mercury dibromide; In tetrahydrofuran; diethyl ether; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/0960-894X(96)00370-8

upstream raw materials:

acetic anhydride

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-3-amino-6-benzyloxymethyl-2-ethoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(allyloxycarbonylamino)-β-D-glucopyranose

((2R,3R,4R,5S,6R)-2-Ethoxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid allyl ester