Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-2-iodomethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-2-iodomethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 162007-82-1
• Molecular Formula: C₁₆H₂₃IO₇S
• Molecular Weight: 486.325

Synonyms:Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-2-iodomethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester

Chemical Property of Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-2-iodomethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester

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Technology Process of Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-2-iodomethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester

There total 2 articles about Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-2-iodomethyl-4,5,6-trimethoxy-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:

methyl 2,3-di-O-methyl-4,6-di-O-(p-toluenesulfonyl)-α-D-glucopyranoside (62847-79-4) → Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-2-iodomethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester (162007-82-1)

Guidance literature:

With sodium iodide; In butanone; Yield given; Heating;

DOI:10.1021/jo00103a007

Reference yield:

methyl 2,3-di-O-methyl-α-D-glucopyranoside (10227-29-9,14048-30-7,22323-70-2,22323-71-3,23397-51-5,27299-05-4,31085-63-9,66808-29-5,66808-32-0,74560-65-9,91176-73-7,94992-18-4,110416-07-4) → Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-2-iodomethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester (162007-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / pyridine

2: NaI / butan-2-one / Heating

With pyridine; sodium iodide; In butanone;

DOI:10.1021/jo00103a007

Reference yield: 23.0%

Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-2-iodomethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester (162007-82-1) → Toluene-4-sulfonic acid (2R,3R,4R,5R,6S)-2-hydroxymethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester + (3aR,5S,6R,7R,7aS)-5,6,7-Trimethoxy-3-nitro-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]isoxazole

Guidance literature:

With n-propyl nitrite; sodium nitrite; In dimethyl sulfoxide; at 50 - 55 ℃; for 6h;

DOI:10.1021/jo00103a007

upstream raw materials:

methyl 2,3-di-O-methyl-4,6-di-O-(p-toluenesulfonyl)-α-D-glucopyranoside

methyl 2,3-di-O-methyl-α-D-glucopyranoside

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