(2S,3S,4S,5R,6R)-3,4,5-Tris-(2,2-dimethyl-propionyloxy)-6-phenethyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-3,4,5-Tris-(2,2-dimethyl-propionyloxy)-6-phenethyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 386211-04-7
• Molecular Formula: C₃₀H₄₄O₁₀
• Molecular Weight: 564.673

Synonyms:(2S,3S,4S,5R,6R)-3,4,5-Tris-(2,2-dimethyl-propionyloxy)-6-phenethyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4S,5R,6R)-3,4,5-Tris-(2,2-dimethyl-propionyloxy)-6-phenethyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2S,3S,4S,5R,6R)-3,4,5-Tris-(2,2-dimethyl-propionyloxy)-6-phenethyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 5 articles about (2S,3S,4S,5R,6R)-3,4,5-Tris-(2,2-dimethyl-propionyloxy)-6-phenethyloxy-tetrahydro-pyran-2-carboxylic acid methyl 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: 88.0%

2-phenylethanol (60-12-8) + methyl 1-deoxy-1-iodo-2,3,4-tri-O-pivaloyl-α-D-glucopyranuronate (313948-92-4) → (2S,3S,4S,5R,6R)-3,4,5-Tris-(2,2-dimethyl-propionyloxy)-6-phenethyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester (386211-04-7)

Guidance literature:

With iodine; copper(l) chloride; In 1,2-dichloro-ethane; at 20 ℃; for 5h;

DOI:10.1021/ol035475k

Reference yield: 85.0%

2-phenylethanol (60-12-8) + methyl 1-bromo-1-desoxy-O2,O3,O4-tri(2,2-dimethyl-1-oxopropyl)-α-D-glucuronate (86448-92-2) → (2S,3S,4S,5R,6R)-3,4,5-Tris-(2,2-dimethyl-propionyloxy)-6-phenethyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester (386211-04-7)

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 16h;

DOI:10.1016/S0040-4039(01)01333-8

Reference yield:

2-phenylethanol (60-12-8) + methyl 1-deoxy-1-iodo-2,3,4-tri-O-pivaloyl-α-D-glucopyranuronate (313948-92-4) → (2S,3S,4S,5R,6R)-3,4,5-Tris-(2,2-dimethyl-propionyloxy)-6-phenethyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester (386211-04-7) + (3aR,5S,6S,7S,7aR)-2-tert-Butyl-6,7-bis-(2,2-dimethyl-propionyloxy)-2-phenethyloxy-tetrahydro-[1,3]dioxolo[4,5-b]pyran-5-carboxylic acid methyl ester

Guidance literature:

With N-iodo-succinimide; iodine; In 1,2-dichloro-ethane; at 0 - 20 ℃;

DOI:10.1021/ol035475k

upstream raw materials:

2-phenylethanol

methyl 1-bromo-1-desoxy-O²,O³,O⁴-tri(2,2-dimethyl-1-oxopropyl)-α-D-glucuronate

methyl 1-deoxy-1-iodo-2,3,4-tri-O-pivaloyl-α-D-glucopyranuronate

methyl O¹,O²,O³,O⁴-tetra(2,2-dimethyl-1-oxopropyl)-β-D-glucuronate

Downstream raw materials:

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-hydroxymethyl-6-phenethyloxy-tetrahydro-pyran-4-yl ester

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