Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester
CAS No.:208524-48-5
Molecular Formula:C₂₈H₄₁NO₁₆
Molecular Weight:647.631
Hs Code.:

Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester

There total 11 articles about Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexyloxy)-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:

: 144685-11-0
methyl 2-acetamido-3,6-di-O-benzyl-β-D-glucopyranoside

: 208524-48-5
Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1) NaH, 15-crown-5 / 1) DMF, RT, 30 min, 2) DMF, 70 deg C, 25 h

2: 90 percent / DMSO, Ac₂O / 18 h / Ambient temperature

3: 81 percent / DBU / toluene / 1 h / 80 °C

4: 44 percent / NaBH₄, CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.33 h / 0 °C

5: 97 percent / pyridine / 2 h / Ambient temperature

6: 60percent aq. AcOH / 11 h / 55 °C

7: pyridine / 5 h / Ambient temperature

8: 1) H₂O, 2) pyridine / 1) DMF, 120 deg C, 3 d, 2) RT, 5 h

9: 1) hydrogen, 1N HCl, 2) pyridine / 1) 10percent Pd/C / 1) EtOH, 3.5 h, RT

With pyridine; hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; 15-crown-5; water; hydrogen; acetic anhydride; sodium hydride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In methanol; dichloromethane; toluene;
DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

Reference yield:

: 142560-73-4
methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

: 208524-48-5
Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 74 percent / NaCNBH₃ / tetrahydrofuran / 1 h / Ambient temperature

2: 1) NaH, 15-crown-5 / 1) DMF, RT, 30 min, 2) DMF, 70 deg C, 25 h

3: 90 percent / DMSO, Ac₂O / 18 h / Ambient temperature

4: 81 percent / DBU / toluene / 1 h / 80 °C

5: 44 percent / NaBH₄, CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.33 h / 0 °C

6: 97 percent / pyridine / 2 h / Ambient temperature

7: 60percent aq. AcOH / 11 h / 55 °C

8: pyridine / 5 h / Ambient temperature

9: 1) H₂O, 2) pyridine / 1) DMF, 120 deg C, 3 d, 2) RT, 5 h

10: 1) hydrogen, 1N HCl, 2) pyridine / 1) 10percent Pd/C / 1) EtOH, 3.5 h, RT

With pyridine; hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; 15-crown-5; water; hydrogen; acetic anhydride; sodium hydride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

Reference yield:

: N-((2R,3R,4R,6R)-4-Benzyloxy-6-benzyloxymethyl-2-methoxy-5-oxo-tetrahydro-pyran-3-yl)-acetamide

: 208524-48-5
Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-6-methoxy-3-((1R,2S,3S,4S,5R)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexyloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 27 percent / L-selectride / tetrahydrofuran / 7 h / refrigeration

2: 1) NaH, 15-crown-5 / 1) DMF, RT, 30 min, 2) DMF, 70 deg C, 25 h

3: 90 percent / DMSO, Ac₂O / 18 h / Ambient temperature

4: 81 percent / DBU / toluene / 1 h / 80 °C

5: 44 percent / NaBH₄, CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.33 h / 0 °C

6: 97 percent / pyridine / 2 h / Ambient temperature

7: 60percent aq. AcOH / 11 h / 55 °C

8: pyridine / 5 h / Ambient temperature

9: 1) H₂O, 2) pyridine / 1) DMF, 120 deg C, 3 d, 2) RT, 5 h

10: 1) hydrogen, 1N HCl, 2) pyridine / 1) 10percent Pd/C / 1) EtOH, 3.5 h, RT

With pyridine; hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; 15-crown-5; water; hydrogen; acetic anhydride; L-Selectride; sodium hydride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R