methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
• CAS No.: 1187445-13-1
• Molecular Formula: C₃₈H₄₈O₉
• Molecular Weight: 648.794

Synonyms:methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Chemical Property of methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Chemical Property:

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Technology Process of methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

There total 12 articles about methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside 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: 52.0%

1,2-anhydro-3,5,6-tri-O-benzyl-4a-carba-α-D-galactofuranose (1187444-83-2) + methyl 2,3-O-isopropylidene-α-L-rhamnoside (14133-63-2) → methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (1187445-13-1) + C66H78O13 (1314871-77-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.carres.2011.04.032

Reference yield: 52.0%

1,2-anhydro-3,5,6-tri-O-benzyl-4a-carba-α-D-galactofuranose (1187444-83-2) + methyl 2,3-O-isopropylidene-α-L-rhamnoside (14133-63-2) → methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (1187445-13-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.06.115

Reference yield:

3,5,6-Tri-O-benzyl-D-glucofuranose (35958-64-6) → methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (1187445-13-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

1.2: 0 °C / pH 7 / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / 0.25 h / 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -60 °C / Inert atmosphere

3.2: -60 - 20 °C / Inert atmosphere

4.1: n-butyllithium / hexane; toluene / 0 - 20 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: hydrogenchloride / water; acetic acid / 2.5 h / 80 °C

6.1: Hoveyda-Grubbs catalyst second generation / toluene / 1 h / 60 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen; triethylamine / ethyl acetate / 2 h / 20 °C / Inert atmosphere

8.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran

9.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; water; acetic acid; ethyl acetate; toluene; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.2: Wittig reaction / 8.1: Mitsunobu reaction;

DOI:10.1016/j.carres.2011.04.032

upstream raw materials:

1,2-anhydro-3,5,6-tri-O-benzyl-4a-carba-α-D-galactofuranose

methyl 2,3-O-isopropylidene-α-L-rhamnoside

(2S,4S,5S,6R)-1,2,4-tri-O-benzyl-3-methyleneoct-7-ene-1,2,4,5,6-pentaol

1,2-di-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-xylohex-4(4a)-enofuranose

Downstream raw materials:

methyl 2-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

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