4-(1,3-Dioxolan-2-yl)-3-oxabutyl 3,4-di-O-benzyl-2-O-[3,4-di-O-benzyl-2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

Base Information

Chemical Name:4-(1,3-Dioxolan-2-yl)-3-oxabutyl 3,4-di-O-benzyl-2-O-[3,4-di-O-benzyl-2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside
CAS No.:176168-86-8
Molecular Formula:C₆₈H₈₀O₁₇
Molecular Weight:1169.37
Hs Code.:

4-(1,3-Dioxolan-2-yl)-3-oxabutyl 3,4-di-O-benzyl-2-O-[3,4-di-O-benzyl-2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

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Chemical Property of 4-(1,3-Dioxolan-2-yl)-3-oxabutyl 3,4-di-O-benzyl-2-O-[3,4-di-O-benzyl-2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

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Technology Process of 4-(1,3-Dioxolan-2-yl)-3-oxabutyl 3,4-di-O-benzyl-2-O-[3,4-di-O-benzyl-2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

There total 9 articles about 4-(1,3-Dioxolan-2-yl)-3-oxabutyl 3,4-di-O-benzyl-2-O-[3,4-di-O-benzyl-2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-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:

: 69980-52-5
2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide

: 176168-86-8
4-(1,3-Dioxolan-2-yl)-3-oxabutyl 3,4-di-O-benzyl-2-O-[3,4-di-O-benzyl-2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: 2,4,6-trimethylpyridine, tetraethylammonium bromide / CH₂Cl₂ / 1 h / Heating

2: NaH / dimethylformamide / 12 h / Ambient temperature

3: H₂SO₄ / acetic acid / 0.33 h

4: ethanolamine / ethyl acetate / 16 h / Ambient temperature

5: K₂CO₃ / CH₂Cl₂ / 12 h

6: 94 percent / molecular sieves 0.4 nm, trimethylsilyl triflate / CH₂Cl₂ / 0.33 h

7: NaOMe / methanol

8: 79 percent / molecular sieves 0.4 nm, trimethylsilyl triflate / CH₂Cl₂ / 0.5 h

9: NaOMe / methanol

10: molecular sieves 0.4 nm, trimethylsilyl triflate / CH₂Cl₂ / 0.5 h

With 2,4,6-trimethyl-pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; tetraethylammonium bromide; sodium methylate; sodium hydride; potassium carbonate; ethanolamine; In methanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1080/07328309608005434

Reference yield:

: 73983-19-4
1,2-di-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-L-mannopyranose

: 176168-86-8
4-(1,3-Dioxolan-2-yl)-3-oxabutyl 3,4-di-O-benzyl-2-O-[3,4-di-O-benzyl-2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: ethanolamine / ethyl acetate / 16 h / Ambient temperature

2: K₂CO₃ / CH₂Cl₂ / 12 h

3: 94 percent / molecular sieves 0.4 nm, trimethylsilyl triflate / CH₂Cl₂ / 0.33 h

4: NaOMe / methanol

5: 79 percent / molecular sieves 0.4 nm, trimethylsilyl triflate / CH₂Cl₂ / 0.5 h

6: NaOMe / methanol

7: molecular sieves 0.4 nm, trimethylsilyl triflate / CH₂Cl₂ / 0.5 h

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; potassium carbonate; ethanolamine; In methanol; dichloromethane; ethyl acetate;
DOI:10.1080/07328309608005434

Reference yield:

: (5S,6R,7R,7aR)-2-Methoxy-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

: 176168-86-8
4-(1,3-Dioxolan-2-yl)-3-oxabutyl 3,4-di-O-benzyl-2-O-[3,4-di-O-benzyl-2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: NaH / dimethylformamide / 12 h / Ambient temperature

2: H₂SO₄ / acetic acid / 0.33 h

3: ethanolamine / ethyl acetate / 16 h / Ambient temperature

4: K₂CO₃ / CH₂Cl₂ / 12 h

5: 94 percent / molecular sieves 0.4 nm, trimethylsilyl triflate / CH₂Cl₂ / 0.33 h

6: NaOMe / methanol

7: 79 percent / molecular sieves 0.4 nm, trimethylsilyl triflate / CH₂Cl₂ / 0.5 h

8: NaOMe / methanol

9: molecular sieves 0.4 nm, trimethylsilyl triflate / CH₂Cl₂ / 0.5 h

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; sodium methylate; sodium hydride; potassium carbonate; ethanolamine; In methanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1080/07328309608005434