N-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7S,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Base Information

Chemical Name:N-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7S,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide
CAS No.:208524-54-3
Molecular Formula:C₄₄H₅₀N₄O₉
Molecular Weight:778.902
Hs Code.:

N-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7S,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Synonyms:N-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7S,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

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Chemical Property of N-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7S,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

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Technology Process of N-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7S,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

There total 7 articles about N-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7S,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide 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: 57.0%

: 208524-53-2
Methanesulfonic acid (2R,4aR,6R,7R,8S,8aR)-6-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-8-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-7-yl ester

: 208524-54-3
N-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7S,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: With sodium azide; In water; N,N-dimethyl-formamide; at 120 ℃; for 19h;
DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

Reference yield:

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

: 208524-54-3
N-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7S,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 6 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: 52 percent / NaBH₄, CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.33 h / 0 °C

5: 77 percent / pyridine, DMAP / 30 h / Ambient temperature

6: 57 percent / NaN₃ / H₂O; dimethylformamide / 19 h / 120 °C

With pyridine; dmap; sodium tetrahydroborate; sodium azide; cerium(III) chloride; 15-crown-5; acetic anhydride; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 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

: 208524-54-3
N-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7S,8R,8aR)-7-Azido-8-benzyloxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Guidance literature:: Multi-step reaction with 7 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: 52 percent / NaBH₄, CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.33 h / 0 °C

6: 77 percent / pyridine, DMAP / 30 h / Ambient temperature

7: 57 percent / NaN₃ / H₂O; dimethylformamide / 19 h / 120 °C

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