(2R,3R,4R,5R,6S)-2-Benzyloxymethyl-3-iodo-4,5,6-trimethoxy-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3R,4R,5R,6S)-2-Benzyloxymethyl-3-iodo-4,5,6-trimethoxy-tetrahydro-pyran
• CAS No.: 120333-20-2
• Molecular Formula: C₁₆H₂₃IO₅
• Molecular Weight: 422.26

Synonyms:(2R,3R,4R,5R,6S)-2-Benzyloxymethyl-3-iodo-4,5,6-trimethoxy-tetrahydro-pyran

Chemical Property of (2R,3R,4R,5R,6S)-2-Benzyloxymethyl-3-iodo-4,5,6-trimethoxy-tetrahydro-pyran

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Technology Process of (2R,3R,4R,5R,6S)-2-Benzyloxymethyl-3-iodo-4,5,6-trimethoxy-tetrahydro-pyran

There total 2 articles about (2R,3R,4R,5R,6S)-2-Benzyloxymethyl-3-iodo-4,5,6-trimethoxy-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: 80.0%

Trifluoro-methanesulfonic acid (2R,3R,4R,5R,6S)-2-benzyloxymethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester → (2R,3R,4R,5R,6S)-2-Benzyloxymethyl-3-iodo-4,5,6-trimethoxy-tetrahydro-pyran (120333-20-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In acetonitrile; at 80 ℃; for 8h;

DOI:10.1021/jo00271a012

Reference yield:

(2R,3S,4S,5R,6S)-2-Benzyloxymethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-ol (120333-19-9) → (2R,3R,4R,5R,6S)-2-Benzyloxymethyl-3-iodo-4,5,6-trimethoxy-tetrahydro-pyran (120333-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂; pyridine

2: 80 percent / tetra-n-butylammonium iodide / acetonitrile / 8 h / 80 °C

With tetra-(n-butyl)ammonium iodide; In pyridine; dichloromethane; acetonitrile;

DOI:10.1021/jo00271a012

Reference yield: 86.0%

(2R,3R,4R,5R,6S)-2-Benzyloxymethyl-3-iodo-4,5,6-trimethoxy-tetrahydro-pyran (120333-20-2) → methyl 6-O-benzyl-4-deoxy-2,3-di-O-methyl-β-L-threo-hex-4-enopyranoside (120333-23-5)

Guidance literature:

With C₈K; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1021/jo00271a012

upstream raw materials:

(2R,3S,4S,5R,6S)-2-Benzyloxymethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-ol

Downstream raw materials:

methyl 6-O-benzyl-3,4-dideoxy-2-O-methyl-α-D-erythro-hex-3-enopyranoside

(Z)-(2R,3S)-6-Benzyloxy-2,3-dimethoxy-hex-4-enal

6-O-benzyl-4,5-dideoxy-2,3-di-O-methyl-L-threo-hex-4-enose

methyl 6-O-benzyl-4-deoxy-2,3-di-O-methyl-β-L-threo-hex-4-enopyranoside

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