(3aR,5R,5aS,8aS,8bR)-5-[(2S,3S,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-phenylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

Base Information

• Chemical Name: (3aR,5R,5aS,8aS,8bR)-5-[(2S,3S,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-phenylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran
• CAS No.: 144101-13-3
• Molecular Formula: C₃₉H₄₈O₁₀S
• Molecular Weight: 708.87

Synonyms:

Chemical Property of (3aR,5R,5aS,8aS,8bR)-5-[(2S,3S,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-phenylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (3aR,5R,5aS,8aS,8bR)-5-[(2S,3S,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-phenylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

There total 4 articles about (3aR,5R,5aS,8aS,8bR)-5-[(2S,3S,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-phenylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 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:

C31H41N2O6PS (144100-92-5,144100-93-6) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → (3aR,5R,5aS,8aS,8bR)-5-[(2R,3S,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-phenylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (144101-13-3,144101-14-4) + (3aR,5R,5aS,8aS,8bR)-5-[(2S,3S,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-phenylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (144101-13-3,144101-14-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 0.166667h; Yield given. Yields of byproduct given;

DOI:10.1246/cl.1992.1511

Reference yield:

C31H41N2O6PS (144100-92-5,144100-93-6) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → (3aR,5R,5aS,8aS,8bR)-5-[(2R,3S,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-phenylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (144101-13-3,144101-14-4) + (3aR,5R,5aS,8aS,8bR)-5-[(2S,3S,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-phenylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (144101-13-3,144101-14-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 0.166667h; Yield given. Yields of byproduct given;

DOI:10.1246/cl.1992.1511

Reference yield:

(2R,3S,4R,5R,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-phenylsulfanyl)-6-methyl-tetrahydro-pyran-2-ol → (3aR,5R,5aS,8aS,8bR)-5-[(2R,3S,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-phenylsulfanyl)-6-methyl-tetrahydro-pyran-2-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (144101-13-3,144101-14-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi, 2.) HMPA / 1.) THF, -78 deg C, 20 min, 2.) -40 deg C, 2 h

2: trimethylsilyl trifluoromethanesulfonate (TMSOTf) / CH₂Cl₂ / 0.17 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1246/cl.1992.1511

upstream raw materials:

C₃₁H₄₁N₂O₆PS

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Downstream raw materials:

(3,4-di-O-benzyl-2,6-dideoxy-α-L-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

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