(S)-2-{1-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-vinyl}-1,4-dioxa-spiro[4.5]decane

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Chemical Name:(S)-2-{1-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-vinyl}-1,4-dioxa-spiro[4.5]decane
CAS No.:286958-22-3
Molecular Formula:C₂₄H₃₄O₅
Molecular Weight:402.531
Hs Code.:

Synonyms:(S)-2-{1-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-vinyl}-1,4-dioxa-spiro[4.5]decane

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Chemical Property of (S)-2-{1-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-vinyl}-1,4-dioxa-spiro[4.5]decane

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Technology Process of (S)-2-{1-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-vinyl}-1,4-dioxa-spiro[4.5]decane

There total 10 articles about (S)-2-{1-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-vinyl}-1,4-dioxa-spiro[4.5]decane 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: 97.0%

: 75-24-1
trimethylaluminum

: 286958-21-2
(S)-1,4-Dioxa-spiro[4.5]decane-2-carboxylic acid (2S,3R)-2-(2-benzyloxy-ethyl)-tetrahydro-pyran-3-yl ester

: 286958-22-3
(S)-2-{1-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-vinyl}-1,4-dioxa-spiro[4.5]decane

Guidance literature:: trimethylaluminum; With bis(cyclopentadienyl)titanium dichloride; In toluene; at 23 ℃; for 72h;

(S)-1,4-Dioxa-spiro[4.5]decane-2-carboxylic acid (2S,3R)-2-(2-benzyloxy-ethyl)-tetrahydro-pyran-3-yl ester; In tetrahydrofuran; toluene; at 0 - 23 ℃;
DOI:10.1246/cl.2000.610

Reference yield:

: 100-39-0
benzyl bromide

: 286958-22-3
(S)-2-{1-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-vinyl}-1,4-dioxa-spiro[4.5]decane

Guidance literature:: Multi-step reaction with 4 steps

1.1: t-BuOK; TBAI

2.1: 6M HCl / tetrahydrofuran

3.1: 99 percent / DCC; DMAP / CH₂Cl₂ / 22 - 24 °C

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

4.2: 97 percent / tetrahydrofuran; toluene / 0 - 23 °C

With hydrogenchloride; dmap; bis(cyclopentadienyl)titanium dichloride; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; toluene; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Esterification / 4.1: complex formation / 4.2: olefination;
DOI:10.1246/cl.2000.610

Reference yield:

: 242808-58-8
(2S,3R)-2-(2-propenyl)-3-hydroxyoxane

: 286958-22-3
(S)-2-{1-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-vinyl}-1,4-dioxa-spiro[4.5]decane

Guidance literature:: Multi-step reaction with 8 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

With hydrogenchloride; dmap; bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 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;
DOI:10.1246/cl.2000.610