Acetic acid (2R,3R,4S,5R,6R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-2,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5R,6R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-2,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester
CAS No.:143416-61-9
Molecular Formula:C₅₁H₅₇NO₁₂
Molecular Weight:876.013
Hs Code.:

Acetic acid (2R,3R,4S,5R,6R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-2,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

Synonyms:Acetic acid (2R,3R,4S,5R,6R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-2,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-2,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5R,6R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-2,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

There total 19 articles about Acetic acid (2R,3R,4S,5R,6R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-2,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-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: 74.0%

: 143416-60-8
benzyl 2-acetamido-3-O-(2-acetyl-4,6-di-O-benzyl-3-O-chloroacetyl-β-D-galactopyranosyl)-4,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

: 143416-61-9
Acetic acid (2R,3R,4S,5R,6R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-2,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

Guidance literature:: With hydrazinium monoacetate; acetic acid; In methanol; for 12h; Ambient temperature;
DOI:10.1016/S0040-4020(01)81568-4

Reference yield:

: 125367-09-1,125367-10-4,128503-34-4,143416-41-5
pent-4-enyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside

: 143416-61-9
Acetic acid (2R,3R,4S,5R,6R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-2,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 96 percent / MeOH / NaOMe

2: 87 percent / imidazole / tetrahydrofuran / 11.5 h / Ambient temperature

3: 84 percent / p-TsOH*H₂O / toluene / 1 h / Ambient temperature

4: 1 h

5: 3.45 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 23 h / Ambient temperature

6: 1.) TBAF, 2.) NaOMe / 1.) THF, r. t., 9 h, 2.) MeOH

7: 1.) NaH, 2.) n-Bu₄NI / 1.) DMF, r. t., 15 min, 2.) r.t., 4 h

8: p-TsOH / methanol / 3 h

9: 412 mg / pyridine / CH₂Cl₂ / 0.17 h / 0 °C

10: 4-dimethylaminopyridine / CH₂Cl₂

11: 68 percent / N-iodo succinimide (NIS), Et₃SiOTf / CH₂Cl₂

12: 74 percent / N₂H₄*HOAc, HOAc / methanol / 12 h / Ambient temperature

With pyridine; 1H-imidazole; methanol; dmap; N-iodo-succinimide; tetrabutyl ammonium fluoride; triethylsilyl trifluoromethyl sulfonate; sodium methylate; hydrazinium monoacetate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)81568-4

Reference yield:

: 188435-38-3
bromide 2,3,4,6-tetra-O-Bz-α-D-galactopyranosyl bromide

: 143416-61-9
Acetic acid (2R,3R,4S,5R,6R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-2,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 74 percent / silver triflate, molecular sieves (4 Angstroem) / CH₂Cl₂ / 0.5 h / -20 °C

2: 96 percent / MeOH / NaOMe

3: 87 percent / imidazole / tetrahydrofuran / 11.5 h / Ambient temperature

4: 84 percent / p-TsOH*H₂O / toluene / 1 h / Ambient temperature

5: 1 h

6: 3.45 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 23 h / Ambient temperature

7: 1.) TBAF, 2.) NaOMe / 1.) THF, r. t., 9 h, 2.) MeOH

8: 1.) NaH, 2.) n-Bu₄NI / 1.) DMF, r. t., 15 min, 2.) r.t., 4 h

9: p-TsOH / methanol / 3 h

10: 412 mg / pyridine / CH₂Cl₂ / 0.17 h / 0 °C

11: 4-dimethylaminopyridine / CH₂Cl₂

12: 68 percent / N-iodo succinimide (NIS), Et₃SiOTf / CH₂Cl₂

13: 74 percent / N₂H₄*HOAc, HOAc / methanol / 12 h / Ambient temperature

With pyridine; 1H-imidazole; methanol; dmap; N-iodo-succinimide; 4 A molecular sieve; tetrabutyl ammonium fluoride; triethylsilyl trifluoromethyl sulfonate; sodium methylate; silver trifluoromethanesulfonate; hydrazinium monoacetate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)81568-4