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

Base Information

• Chemical Name: (S)-1,4-Dioxa-spiro[4.5]decane-2-carboxylic acid (2S,3R)-2-(2-benzyloxy-ethyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 286958-21-2
• Molecular Formula: C₂₃H₃₂O₆
• Molecular Weight: 404.503
• Mol file: 286958-21-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (S)-1,4-Dioxa-spiro[4.5]decane-2-carboxylic acid (2S,3R)-2-(2-benzyloxy-ethyl)-tetrahydro-pyran-3-yl 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: 99.0%

(S)-1,4-Dioxa-spiro[4.5]decane-2-carboxylic acid + (2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-ol (286958-05-2) → (S)-1,4-Dioxa-spiro[4.5]decane-2-carboxylic acid (2S,3R)-2-(2-benzyloxy-ethyl)-tetrahydro-pyran-3-yl ester (286958-21-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 22 - 24 ℃;

DOI:10.1246/cl.2000.610

Reference yield:

benzyl bromide (100-39-0) → (S)-1,4-Dioxa-spiro[4.5]decane-2-carboxylic acid (2S,3R)-2-(2-benzyloxy-ethyl)-tetrahydro-pyran-3-yl ester (286958-21-2)

Guidance literature:

Multi-step reaction with 3 steps

1: t-BuOK; TBAI

2: 6M HCl / tetrahydrofuran

3: 99 percent / DCC; DMAP / CH₂Cl₂ / 22 - 24 °C

With hydrogenchloride; dmap; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 1: Etherification / 2: Hydrolysis / 3: Esterification;

DOI:10.1246/cl.2000.610

Reference yield:

(2S,3R)-2-(2-propenyl)-3-hydroxyoxane (242808-58-8) → (S)-1,4-Dioxa-spiro[4.5]decane-2-carboxylic acid (2S,3R)-2-(2-benzyloxy-ethyl)-tetrahydro-pyran-3-yl ester (286958-21-2)

Guidance literature:

Multi-step reaction with 7 steps

1: i-Pr₂NEt

2: OsO₄; NMO

3: NaIO₄

4: NaBH₄

5: t-BuOK; TBAI

6: 6M HCl / tetrahydrofuran

7: 99 percent / DCC; DMAP / CH₂Cl₂ / 22 - 24 °C

With hydrogenchloride; dmap; 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; 1: Etherification / 2: dihydroxylation / 3: oxidative cleavage / 4: Reduction / 5: Etherification / 6: Hydrolysis / 7: Esterification;

DOI:10.1246/cl.2000.610

upstream raw materials:

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

benzyl bromide

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

Downstream raw materials:

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

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

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

(S)-2-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-ethanol