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

Base Information

• Chemical Name: 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
• CAS No.: 208524-53-2
• Molecular Formula: C₄₅H₅₃NO₁₂S
• Molecular Weight: 831.981

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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: 77.0%

methanesulfonyl chloride (124-63-0) + N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-5-((2R,4aR,6R,7R,8R,8aR)-8-benzyloxy-7-hydroxy-2-phenyl-hexahydro-benzo[1,3]dioxin-6-yloxy)-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (208524-45-2) → 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 (208524-53-2)

Guidance literature:

With pyridine; dmap; for 30h; Ambient temperature;

DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

Reference yield:

methyl 2-acetamido-3,6-di-O-benzyl-β-D-glucopyranoside (144685-11-0) → 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 (208524-53-2)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; 15-crown-5; acetic anhydride; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 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 → 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 (208524-53-2)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; dmap; sodium tetrahydroborate; 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; toluene;

DOI:10.1002/(SICI)1099-0690(199806)1998:6<1099::AID-EJOC1099<3.0.CO;2-R

upstream raw materials:

methanesulfonyl chloride

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

methyl 2-acetamido-3,6-di-O-benzyl-β-D-glucopyranoside

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

Downstream raw materials:

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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