(2S,3R,4R,5S)-4-Allyloxy-3-benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran

Base Information

• Chemical Name: (2S,3R,4R,5S)-4-Allyloxy-3-benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran
• CAS No.: 141505-59-1
• Molecular Formula: C₁₈H₂₆O₅
• Molecular Weight: 322.401

Synonyms:(2S,3R,4R,5S)-4-Allyloxy-3-benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran

Chemical Property of (2S,3R,4R,5S)-4-Allyloxy-3-benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Technology Process of (2S,3R,4R,5S)-4-Allyloxy-3-benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran

There total 2 articles about (2S,3R,4R,5S)-4-Allyloxy-3-benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran 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: 90.0%

benzyl bromide (100-39-0) + (2S,3R,4R,5S)-4-Allyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-ol (141418-24-8) → (2S,3R,4R,5S)-4-Allyloxy-3-benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran (141505-59-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 18h; Ambient temperature;

DOI:10.1016/0008-6215(92)84070-9

Reference yield:

Methyl 2-O-methyl-L-fucopyranoside (29836-35-9) → (2S,3R,4R,5S)-4-Allyloxy-3-benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran (141505-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) dibutyltin oxide, 2) Bu₄NI / 1) benzene, reflux, 5 h, 2) reflux, 5 h

2: 90 percent / NaH / tetrahydrofuran / 18 h / Ambient temperature

With tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran;

DOI:10.1016/0008-6215(92)84070-9

Reference yield:

(2S,3R,4R,5S)-4-Allyloxy-3-benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran (141505-59-1) → (3S,4R,5R,6S)-4-Allyloxy-5-benzyloxy-3-methoxy-6-methyl-tetrahydro-pyran-2-ol

Guidance literature:

With sulfuric acid; In 1,4-dioxane; at 100 ℃; for 4h;

DOI:10.1016/0008-6215(92)84070-9

upstream raw materials:

benzyl bromide

(2S,3R,4R,5S)-4-Allyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-ol

Methyl 2-O-methyl-L-fucopyranoside

Downstream raw materials:

Methyl 3-O-<4-O-benzyl-3-O-(4-O-benzyl-2-O-methyl-α-L-fucopyranosyl)-2-O-methyl-α-L-rhamnopyranosyl>-2,4-di-O-methyl-α-L-rhamnopyranoside

Methyl 3-O-<3-O-(3-O-allyl-4-O-benzyl-2-O-methyl-α-L-fucopyranosyl)-4-O-benzyl-2-O-methyl-α-L-rhamnopyranosyl>-2,4-di-O-methyl-α-L-rhamnopyranoside

1-O-Acetyl-3-O-allyl-4-O-benzyl-2-O-methyl-α,β-L-fucose

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