(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 141607-25-2
• Molecular Formula: C₂₆H₂₉O₁₃P
• Molecular Weight: 580.482

Synonyms:(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 7 articles about (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 94.0%

2,3,4,6-tetra-O-acetyl-D-mannopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1) + chlorophosphoric acid diphenyl ester (2524-64-3) → (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (141607-25-2)

Guidance literature:

With dmap; In dichloromethane; 1) -30 deg C, 1 h, 2) -10 to 0 deg C, 2 h;

DOI:10.1016/0008-6215(92)80015-S

Reference yield: 52.1%

2,3,4,6-tetra-O-acetyl-D-mannopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1) + chlorophosphoric acid diphenyl ester (2524-64-3) → (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (139710-25-1) + (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (141607-25-2)

Guidance literature:

With dmap; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(92)80015-S

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (22860-22-6) + chlorophosphoric acid diphenyl ester (2524-64-3) → (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (141607-25-2)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, -78 deg C, 25 min;

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-mannopyranose

chlorophosphoric acid diphenyl ester

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose

per-O-acetyl-α-D-mannopyranose

Downstream raw materials:

erythro-N^α-((benzyloxy)carbonyl)-N^im-(triphenylmethyl)-β-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-histidine methyl ester

(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(2-(2-(((benzyloxy)carbonyl)amino)ethoxy) ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

N^α-((tert-butyloxy)carbonyl)-1-<<4(S)-(((1(S)-(((2-(4'-(((3-(dimethylsulfonio)-1-propyl)amino)carbonyl)-2',4-bithiazol-2-yl)-1-ethyl)amino)carbonyl)-2(R)-hydroxy-1-propyl)amino)carbonyl)-3(S)-hydroxy-2(R)-pentyl>amino>-N^im-(triphenylmethyl)-erythr

1-<<4(S)-(((1(S)-(((2-(4'-(((3-(dimethylsulfonio)-1-propyl)amino)carbonyl)-2',4-bithiazol-2-yl)1-ethyl)amino)carbonyl)-2(R)-hydroxy-1-propyl)amino)carbonyl)-3(S)-hydroxy-2(R)-pentyl>amino>-N^im-(triphenylmethyl)erythro-β-(α-D-gulopyranosyl)-L-histidi

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