methyl 2-O-allyl-4-O-benzyl-3-O-[4-O-benzyl-3-O-methyl-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

Base Information

Chemical Name:methyl 2-O-allyl-4-O-benzyl-3-O-[4-O-benzyl-3-O-methyl-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside
CAS No.:192325-16-9
Molecular Formula:C₅₈H₇₀O₁₃
Molecular Weight:975.186
Hs Code.:

Synonyms:methyl 2-O-allyl-4-O-benzyl-3-O-[4-O-benzyl-3-O-methyl-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

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Chemical Property of methyl 2-O-allyl-4-O-benzyl-3-O-[4-O-benzyl-3-O-methyl-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

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Technology Process of methyl 2-O-allyl-4-O-benzyl-3-O-[4-O-benzyl-3-O-methyl-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

There total 7 articles about methyl 2-O-allyl-4-O-benzyl-3-O-[4-O-benzyl-3-O-methyl-2-O-(2,3,4-tri-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: 85.0%

: 100-39-0
benzyl bromide

: 192325-15-8
(2S,3R,4R,5R,6S)-2-[(2S,3R,4R,5S,6S)-2-((2R,3R,4R,5S,6S)-3-Allyloxy-5-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-benzyloxy-4-methoxy-6-methyl-tetrahydro-pyran-3-yloxy]-6-methyl-tetrahydro-pyran-3,4,5-triol

: 192325-16-9
methyl 2-O-allyl-4-O-benzyl-3-O-[4-O-benzyl-3-O-methyl-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

Guidance literature:: With sodium hydride; In tetrahydrofuran; paraffin; for 12h; Ambient temperature;
DOI:10.1016/S0040-4020(97)00532-2

Reference yield:

: 25019-69-6
methyl 4-O-benzyl-α-L-rhamnopyranoside

: 192325-16-9
methyl 2-O-allyl-4-O-benzyl-3-O-[4-O-benzyl-3-O-methyl-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / 5percent NaOH, Bu₄NBr / CH₂Cl₂ / 6 h / Ambient temperature

2: 90 percent / 4A MS, BF₃*OEt₂ / CH₂Cl₂ / 3 h / Ambient temperature

3: 95 percent / NaOMe / methanol / 1 h / Ambient temperature

4: 85 percent / 4A MS, BF₃*OEt₂ / CH₂Cl₂ / 3 h / Ambient temperature

5: NaOMe / methanol / 1 h / Ambient temperature

6: 85 percent / NaH / tetrahydrofuran; paraffin / 12 h / Ambient temperature

With sodium hydroxide; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; paraffin;
DOI:10.1016/S0040-4020(97)00532-2

Reference yield:

: 69558-08-3
methyl 2-O-allyl-4-O-benzyl-α-L-rhamnopyranoside

: 192325-16-9
methyl 2-O-allyl-4-O-benzyl-3-O-[4-O-benzyl-3-O-methyl-2-O-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / 4A MS, BF₃*OEt₂ / CH₂Cl₂ / 3 h / Ambient temperature

2: 95 percent / NaOMe / methanol / 1 h / Ambient temperature

3: 85 percent / 4A MS, BF₃*OEt₂ / CH₂Cl₂ / 3 h / Ambient temperature

4: NaOMe / methanol / 1 h / Ambient temperature

5: 85 percent / NaH / tetrahydrofuran; paraffin / 12 h / Ambient temperature

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; paraffin;
DOI:10.1016/S0040-4020(97)00532-2