{(2R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.4]non-2-yl}-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanone

Base Information

Chemical Name:{(2R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.4]non-2-yl}-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanone
CAS No.:692734-45-5
Molecular Formula:C₃₂H₅₀O₈Si
Molecular Weight:590.83
Hs Code.:

{(2R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.4]non-2-yl}-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanone

Synonyms:{(2R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.4]non-2-yl}-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanone

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Chemical Property of {(2R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.4]non-2-yl}-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanone

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Technology Process of {(2R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.4]non-2-yl}-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanone

There total 10 articles about {(2R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.4]non-2-yl}-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanone 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:

: 607358-63-4
(2R,3R)-[3-(4'-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanol

: 692734-45-5
{(2R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.4]non-2-yl}-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanone

Guidance literature:: Multi-step reaction with 6 steps

1.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C

2.2: ClTi(Oi-Pr)3 / tetrahydrofuran; hexane / 1.5 h / -60 °C

2.3: tetrahydrofuran; hexane / 2 h / -78 - -50 °C

3.1: 747 mg / Red-Al(R) / tetrahydrofuran; toluene / 0 - 20 °C

4.1: 86 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0 - 20 °C

5.1: (DHQ)2-PHAL; K₃[Fe(CN)6]; K₂OsO₄*2H₂O / NaHCO₃; CH₃SO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 22 h / 0 °C

6.1: TsOH*H₂O / CH₂Cl₂ / 2 h / 0 °C

With potassium osmate(VI); n-butyllithium; oxalyl dichloride; (DHQ)2-PHAL; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; potassium hexacyanoferrate(III); methanesulfonamide; sodium hydrogencarbonate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 1.1: Moffat-Swern oxidation / 5.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ja0533646

Reference yield:

: 692734-63-7
(2S,3R)-3-(4-Methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]nonane-2-carbaldehyde

: 692734-45-5
{(2R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.4]non-2-yl}-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C

1.2: ClTi(Oi-Pr)3 / tetrahydrofuran; hexane / 1.5 h / -60 °C

1.3: tetrahydrofuran; hexane / 2 h / -78 - -50 °C

2.1: 747 mg / Red-Al(R) / tetrahydrofuran; toluene / 0 - 20 °C

3.1: 86 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0 - 20 °C

4.1: (DHQ)2-PHAL; K₃[Fe(CN)6]; K₂OsO₄*2H₂O / NaHCO₃; CH₃SO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 22 h / 0 °C

5.1: TsOH*H₂O / CH₂Cl₂ / 2 h / 0 °C

With potassium osmate(VI); n-butyllithium; (DHQ)2-PHAL; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; potassium hexacyanoferrate(III); methanesulfonamide; sodium hydrogencarbonate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 4.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ja0533646

Reference yield:

: 692734-53-5
(E)-5-(tert-Butyl-dimethyl-silanyloxy)-1-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-pent-2-en-1-one

: 692734-45-5
{(2R,3S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1,4-dioxa-spiro[4.4]non-2-yl}-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanone

Guidance literature:: Multi-step reaction with 2 steps

1: (DHQ)2-PHAL; K₃[Fe(CN)6]; K₂OsO₄*2H₂O / NaHCO₃; CH₃SO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 22 h / 0 °C

2: TsOH*H₂O / CH₂Cl₂ / 2 h / 0 °C

With potassium osmate(VI); (DHQ)2-PHAL; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); methanesulfonamide; sodium hydrogencarbonate; In dichloromethane; water; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ja0533646