Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-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-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-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-yl ester
• CAS No.: 192325-14-7
• Molecular Formula: C₄₃H₅₈O₁₆
• Molecular Weight: 830.924

Synonyms:Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-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-yl ester

Chemical Property of Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-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-yl ester

Chemical Property:

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Technology Process of Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-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-yl ester

There total 5 articles about Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-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-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: 85.0%

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (122089-71-8) + methyl 2-O-allyl-4-O-benzyl-3-O-(4-O-benzyl-3-O-methyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside (192325-13-6) → Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-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-yl ester (192325-14-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00532-2

Reference yield:

methyl 4-O-benzyl-α-L-rhamnopyranoside (25019-69-6) → Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-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-yl ester (192325-14-7)

Guidance literature:

Multi-step reaction with 4 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

With sodium hydroxide; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(97)00532-2

Reference yield:

methyl 2-O-allyl-4-O-benzyl-α-L-rhamnopyranoside (69558-08-3) → Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-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-yl ester (192325-14-7)

Guidance literature:

Multi-step reaction with 3 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

With boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(97)00532-2

upstream raw materials:

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

methyl 2-O-allyl-4-O-benzyl-3-O-(4-O-benzyl-3-O-methyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

methyl 4-O-benzyl-α-L-rhamnopyranoside

methyl 2-O-allyl-4-O-benzyl-α-L-rhamnopyranoside

Downstream raw materials:

C₆₆H₈₀O₂₀

C₆₀H₇₄O₁₇

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

methyl 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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