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

Base Information

Chemical Name:(R)-2-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-2-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-ethanol
CAS No.:286958-08-5
Molecular Formula:C₂₄H₃₆O₆
Molecular Weight:420.546
Hs Code.:

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

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

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

There total 11 articles about (R)-2-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-2-(R)-1,4-dioxa-spiro[4.5]dec-2-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: 57.0%

: 286958-07-4
(R)-2-{1-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-vinyl}-1,4-dioxa-spiro[4.5]decane

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

: 286958-08-5
(R)-2-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-2-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-ethanol

Guidance literature:: (R)-2-{1-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-vinyl}-1,4-dioxa-spiro[4.5]decane; With borane-THF; In tetrahydrofuran; at -30 ℃; for 14h;

With sodium hydroxide; dihydrogen peroxide; at 0 - 25 ℃; for 11h;
DOI:10.1246/cl.2000.610

Reference yield:

: 100-39-0
benzyl bromide

: 286958-08-5
(R)-2-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-2-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-ethanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: t-BuOK; TBAI

2.1: 6M HCl / tetrahydrofuran

3.1: 100 percent / DCC; DMAP / CH₂Cl₂ / 22 - 24 °C

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

4.2: 100 percent / tetrahydrofuran; toluene / 0 - 23 °C

5.1: BH₃*THF / tetrahydrofuran / 14 h / -30 °C

5.2: 57 percent / 5M NaOH; 30 percent H₂O₂ / 11 h / 0 - 25 °C

With hydrogenchloride; dmap; bis(cyclopentadienyl)titanium dichloride; borane-THF; 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 / 5.1: hydroboration / 5.2: Oxidation;
DOI:10.1246/cl.2000.610

Reference yield:

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

: 286958-08-5
(R)-2-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-2-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-ethanol

Guidance literature:: Multi-step reaction with 9 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: 100 percent / DCC; DMAP / CH₂Cl₂ / 22 - 24 °C

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

8.2: 100 percent / tetrahydrofuran; toluene / 0 - 23 °C

9.1: BH₃*THF / tetrahydrofuran / 14 h / -30 °C

9.2: 57 percent / 5M NaOH; 30 percent H₂O₂ / 11 h / 0 - 25 °C

With hydrogenchloride; dmap; bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; borane-THF; 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 / 9.1: hydroboration / 9.2: Oxidation;
DOI:10.1246/cl.2000.610