[(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid

Base Information

• Chemical Name: [(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid
• CAS No.: 1262295-42-0
• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.455

Synonyms:[(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid

Chemical Property of [(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid

Chemical Property:

Purity/Quality:

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Technology Process of [(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid

There total 15 articles about [(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid 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: 93.0%

[(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester (1262295-40-8) → [(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid (1262295-42-0)

Guidance literature:

[(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester; With lithium hydroxide monohydrate; water; In tetrahydrofuran; methanol; at 20 ℃; for 20h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; methanol; water; Inert atmosphere;

DOI:10.1021/jo101782q

Reference yield:

[(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-tert-butyl-dimethyl-silane (1262295-46-4) → [(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid (1262295-42-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 - 60 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

3.1: toluene / 48 h / Reflux; Inert atmosphere

4.1: toluene-4-sulfonic acid / chloroform / 20 h / Reflux; Inert atmosphere

5.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 20 h / 20 °C / Inert atmosphere

5.2: Inert atmosphere

With oxalyl dichloride; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Horner-Wittig reaction / 4.1: oxa-Michael cyclization;

DOI:10.1021/jo101782q

Reference yield:

(3R,5R,7S)-7-benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-8,8-dimethyl-nonane-3,5-diol (1262295-45-3) → [(2S,4S,6R)-4-benzyloxy-6-((R)-2-hydroxy-butyl)-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid (1262295-42-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 - 60 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

4.1: toluene / 48 h / Reflux; Inert atmosphere

5.1: toluene-4-sulfonic acid / chloroform / 20 h / Reflux; Inert atmosphere

6.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 20 h / 20 °C / Inert atmosphere

6.2: Inert atmosphere

With oxalyl dichloride; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Horner-Wittig reaction / 5.1: oxa-Michael cyclization;

DOI:10.1021/jo101782q

upstream raw materials:

(5S,7S)-7-benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8,8-dimethyl-nonan-3-one

(3R,5R,7S)-7-benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-8,8-dimethyl-nonane-3,5-diol

[(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-tert-butyl-dimethyl-silane

(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butan-1-ol

Downstream raw materials:

(1S,5R,7R,9S,11S,15R,17R,19S)-9,19-bis-benzyloxy-5,15-diethyl-10,10,20,20-tetramethyl-4,14,21,22-tetraoxa-tricyclo[15.3.1.1(7,11)]docosane-3,13-dione

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