Benzoic acid (S)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2-[(2S,3R)-2-(2-oxo-ethyl)-tetrahydro-pyran-3-yloxy]-ethyl ester

Base Information

• Chemical Name: Benzoic acid (S)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2-[(2S,3R)-2-(2-oxo-ethyl)-tetrahydro-pyran-3-yloxy]-ethyl ester
• CAS No.: 286958-15-4
• Molecular Formula: C₂₄H₃₂O₇
• Molecular Weight: 432.514

Synonyms:Benzoic acid (S)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2-[(2S,3R)-2-(2-oxo-ethyl)-tetrahydro-pyran-3-yloxy]-ethyl ester

Chemical Property of Benzoic acid (S)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2-[(2S,3R)-2-(2-oxo-ethyl)-tetrahydro-pyran-3-yloxy]-ethyl ester

Chemical Property:

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Technology Process of Benzoic acid (S)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2-[(2S,3R)-2-(2-oxo-ethyl)-tetrahydro-pyran-3-yloxy]-ethyl ester

There total 13 articles about Benzoic acid (S)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2-[(2S,3R)-2-(2-oxo-ethyl)-tetrahydro-pyran-3-yloxy]-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: 96.0%

Benzoic acid (S)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2-[(2S,3R)-2-(2-hydroxy-ethyl)-tetrahydro-pyran-3-yloxy]-ethyl ester (286958-14-3) → Benzoic acid (S)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2-[(2S,3R)-2-(2-oxo-ethyl)-tetrahydro-pyran-3-yloxy]-ethyl ester (286958-15-4)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃; for 0.916667h;

DOI:10.1246/cl.2000.610

Reference yield:

(2S,3R)-2-(2-propenyl)-3-hydroxyoxane (242808-58-8) → Benzoic acid (S)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2-[(2S,3R)-2-(2-oxo-ethyl)-tetrahydro-pyran-3-yloxy]-ethyl ester (286958-15-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: i-Pr₂NEt

2.1: OsO₄; NMO

3.1: NaIO₄

4.1: NaBH₄

5.1: t-BuOK; TBAI

6.1: 6M HCl / tetrahydrofuran

7.1: 99 percent / DCC; DMAP / CH₂Cl₂ / 22 - 24 °C

8.1: Cp₂TiCl₂ / toluene / 72 h / 23 °C

8.2: 97 percent / tetrahydrofuran; toluene / 0 - 23 °C

9.1: BH₃*THF / tetrahydrofuran / 0.67 h / 0 °C

9.2: 79 percent / 5M NaOH; 30 percent H₂O₂ / 13 h / 0 - 22 °C

10.1: DMAP / pyridine / 3.5 h / 25 °C

11.1: H₂ / Pd/C / ethanol / 22 - 25 °C

12.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.92 h / -78 - 0 °C

With hydrogenchloride; dmap; bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; borane-THF; oxalyl dichloride; potassium tert-butylate; hydrogen; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; toluene; 1.1: Etherification / 2.1: dihydroxylation / 3.1: oxidative cleavage / 4.1: Reduction / 5.1: Etherification / 6.1: Hydrolysis / 7.1: Esterification / 8.1: complex formation / 8.2: olefination / 9.1: hydroboration / 9.2: Oxidation / 10.1: Esterification / 11.1: debenzylation / 12.1: Oxidation;

DOI:10.1246/cl.2000.610

Reference yield:

((2S,3R)-3-Methoxymethoxy-tetrahydro-pyran-2-yl)-acetaldehyde → Benzoic acid (S)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2-[(2S,3R)-2-(2-oxo-ethyl)-tetrahydro-pyran-3-yloxy]-ethyl ester (286958-15-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaBH₄

2.1: t-BuOK; TBAI

3.1: 6M HCl / tetrahydrofuran

4.1: 99 percent / DCC; DMAP / CH₂Cl₂ / 22 - 24 °C

5.1: Cp₂TiCl₂ / toluene / 72 h / 23 °C

5.2: 97 percent / tetrahydrofuran; toluene / 0 - 23 °C

6.1: BH₃*THF / tetrahydrofuran / 0.67 h / 0 °C

6.2: 79 percent / 5M NaOH; 30 percent H₂O₂ / 13 h / 0 - 22 °C

7.1: DMAP / pyridine / 3.5 h / 25 °C

8.1: H₂ / Pd/C / ethanol / 22 - 25 °C

9.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.92 h / -78 - 0 °C

With hydrogenchloride; dmap; bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; borane-THF; oxalyl dichloride; potassium tert-butylate; hydrogen; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; toluene; 1.1: Reduction / 2.1: Etherification / 3.1: Hydrolysis / 4.1: Esterification / 5.1: complex formation / 5.2: olefination / 6.1: hydroboration / 6.2: Oxidation / 7.1: Esterification / 8.1: debenzylation / 9.1: Oxidation;

DOI:10.1246/cl.2000.610

upstream raw materials:

Benzoic acid (S)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2-[(2S,3R)-2-(2-hydroxy-ethyl)-tetrahydro-pyran-3-yloxy]-ethyl ester

(2S,3R)-2-(2-propenyl)-3-hydroxyoxane

(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-ol

(S)-1,4-Dioxa-spiro[4.5]decane-2-carboxylic acid (2S,3R)-2-(2-benzyloxy-ethyl)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

Benzoic acid (R)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-but-3-enyl ester

Benzoic acid (S)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-ethyl ester

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