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

Base Information

• Chemical Name: Benzoic acid (S)-2-benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethyl ester
• CAS No.: 900792-41-8
• Molecular Formula: C₂₉H₃₂O₆S
• Molecular Weight: 508.635

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

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

Chemical Property:

Purity/Quality:

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

There total 4 articles about Benzoic acid (S)-2-benzyloxy-1-[(4S,5R)-2,2-dimethyl-5-((S)-toluene-4-sulfinylmethyl)-[1,3]dioxolan-4-yl]-ethyl 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%

Benzoic acid (1S,2R,3R)-1-benzyloxymethyl-2,3-dihydroxy-4-((S)-toluene-4-sulfinyl)-butyl ester (900792-40-7) + 2,2-dimethoxy-propane (77-76-9) → 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)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane;

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) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / titanium tetraisopropoxide

2: 88 percent / CSA / CH₂Cl₂

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

DOI:10.1016/j.tetlet.2006.05.043

Reference yield:

benzoic acid (65-85-0,8013-63-6) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / titanium tetraisopropoxide

2: 88 percent / CSA / CH₂Cl₂

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

DOI:10.1016/j.tetlet.2006.05.043

upstream raw materials:

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

2,2-dimethoxy-propane

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

benzoic acid

Downstream raw materials:

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

{(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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