(2R,3R,4R,5R,6S)-3-Benzyloxy-5,6-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-4-carbonitrile

Base Information

• Chemical Name: (2R,3R,4R,5R,6S)-3-Benzyloxy-5,6-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-4-carbonitrile
• CAS No.: 82742-22-1
• Molecular Formula: C₁₄H₁₇NO₅
• Molecular Weight: 279.293

Synonyms:(2R,3R,4R,5R,6S)-3-Benzyloxy-5,6-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-4-carbonitrile

Chemical Property of (2R,3R,4R,5R,6S)-3-Benzyloxy-5,6-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-4-carbonitrile

Chemical Property:

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Technology Process of (2R,3R,4R,5R,6S)-3-Benzyloxy-5,6-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-4-carbonitrile

There total 1 articles about (2R,3R,4R,5R,6S)-3-Benzyloxy-5,6-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-4-carbonitrile 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 (3R,4S,5R,6R)-2-acetoxy-6-acetoxymethyl-5-benzyloxy-4-cyano-tetrahydro-pyran-3-yl ester (82752-60-1) → (2R,3R,4R,5R,6S)-3-Benzyloxy-5,6-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-4-carbonitrile (82742-22-1)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1021/jo00143a018

Reference yield: 70.0%

(2R,3R,4R,5R,6S)-3-Benzyloxy-5,6-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-4-carbonitrile (82742-22-1) + 2,2-dimethoxy-propane (77-76-9) → 4-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-galactopyranose (82742-23-2)

Guidance literature:

With toluene-4-sulfonic acid; In 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/jo00143a018

Reference yield:

methanol (67-56-1) + (2R,3R,4R,5R,6S)-3-Benzyloxy-5,6-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-4-carbonitrile (82742-22-1) + 2,2-dimethoxy-propane (77-76-9) → (1S)-4-O-benzyl-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-1-O-methyl-D-galactose (82795-70-8) + (1R)-4-O-benzyl-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-1-O-methyl-D-galactose (82742-24-3)

Guidance literature:

With toluene-4-sulfonic acid; for 5h; Ambient temperature;

DOI:10.1021/jo00143a018

upstream raw materials:

Acetic acid (3R,4S,5R,6R)-2-acetoxy-6-acetoxymethyl-5-benzyloxy-4-cyano-tetrahydro-pyran-3-yl ester

Downstream raw materials:

(1S)-4-O-benzyl-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-1-O-methyl-D-galactose

(1R)-4-O-benzyl-3-C-cyano-3-deoxy-1,2:5,6-di-O-isopropylidene-1-O-methyl-D-galactose

4-O-benzyl-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-galactopyranose

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