(S)-2-Benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethanol

Base Information

• Chemical Name: (S)-2-Benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethanol
• CAS No.: 900792-42-9
• Molecular Formula: C₂₂H₂₈O₅S
• Molecular Weight: 404.527

Synonyms:(S)-2-Benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethanol

Chemical Property of (S)-2-Benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethanol

Chemical Property:

Purity/Quality:

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Technology Process of (S)-2-Benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethanol

There total 4 articles about (S)-2-Benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethanol 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: 91.0%

Benzoic acid (S)-2-benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethyl ester (900792-41-8) → (S)-2-Benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethanol (900792-42-9)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2006.05.043

Reference yield:

(R)-1-((2R,3R)-3-Benzyloxymethyl-oxiranyl)-2-((S)-toluene-4-sulfinyl)-ethanol (900792-39-4) → (S)-2-Benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethanol (900792-42-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / titanium tetraisopropoxide

2: 88 percent / CSA / CH₂Cl₂

3: 91 percent / DIBAL-H / tetrahydrofuran

With titanium(IV) isopropylate; camphor-10-sulfonic acid; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; 1: Sharpless protocol;

DOI:10.1016/j.tetlet.2006.05.043

Reference yield:

Benzoic acid (1S,2R,3R)-1-benzyloxymethyl-2,3-dihydroxy-4-((S)-toluene-4-sulfinyl)-butyl ester (900792-40-7) → (S)-2-Benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethanol (900792-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / CSA / CH₂Cl₂

2: 91 percent / DIBAL-H / tetrahydrofuran

With camphor-10-sulfonic acid; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2006.05.043

upstream raw materials:

Benzoic acid (S)-2-benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethyl ester

(R)-1-((2R,3R)-3-Benzyloxymethyl-oxiranyl)-2-((S)-toluene-4-sulfinyl)-ethanol

Benzoic acid (1S,2R,3R)-1-benzyloxymethyl-2,3-dihydroxy-4-((S)-toluene-4-sulfinyl)-butyl ester

5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol

Downstream raw materials:

{(S)-2-Benzyloxy-1-[(4R,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethoxy}-tert-butyl-dimethyl-silane

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