(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

Base Information

• Chemical Name: (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
• CAS No.: 192325-15-8
• Molecular Formula: C₃₇H₅₂O₁₃
• Molecular Weight: 704.812

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (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

There total 6 articles about (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 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:

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) → (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 (192325-15-8)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

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

Reference yield:

methyl 4-O-benzyl-α-L-rhamnopyranoside (25019-69-6) → (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 (192325-15-8)

Guidance literature:

Multi-step reaction with 5 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

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) → (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 (192325-15-8)

Guidance literature:

Multi-step reaction with 4 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

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

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

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

C₆₆H₈₀O₂₀

C₆₀H₇₄O₁₇

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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