tert-butyl(2-{(2S,3S)-3-[1-((2R,3R)-3-{[(4-methoxybenzyl)oxy]methyl}-1,4-dioxaspiro[4.4]non-2-yl)vinyl]-1,4-dioxaspiro[4.4]non-2-yl}ethoxy)dimethylsilane

Base Information

• Chemical Name: tert-butyl(2-{(2S,3S)-3-[1-((2R,3R)-3-{[(4-methoxybenzyl)oxy]methyl}-1,4-dioxaspiro[4.4]non-2-yl)vinyl]-1,4-dioxaspiro[4.4]non-2-yl}ethoxy)dimethylsilane
• CAS No.: 692734-54-6
• Molecular Formula: C₃₃H₅₂O₇Si
• Molecular Weight: 588.857
• Mol file: 692734-54-6.mol

Synonyms:tert-butyl(2-{(2S,3S)-3-[1-((2R,3R)-3-{[(4-methoxybenzyl)oxy]methyl}-1,4-dioxaspiro[4.4]non-2-yl)vinyl]-1,4-dioxaspiro[4.4]non-2-yl}ethoxy)dimethylsilane

Chemical Property of tert-butyl(2-{(2S,3S)-3-[1-((2R,3R)-3-{[(4-methoxybenzyl)oxy]methyl}-1,4-dioxaspiro[4.4]non-2-yl)vinyl]-1,4-dioxaspiro[4.4]non-2-yl}ethoxy)dimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl(2-{(2S,3S)-3-[1-((2R,3R)-3-{[(4-methoxybenzyl)oxy]methyl}-1,4-dioxaspiro[4.4]non-2-yl)vinyl]-1,4-dioxaspiro[4.4]non-2-yl}ethoxy)dimethylsilane

There total 12 articles about tert-butyl(2-{(2S,3S)-3-[1-((2R,3R)-3-{[(4-methoxybenzyl)oxy]methyl}-1,4-dioxaspiro[4.4]non-2-yl)vinyl]-1,4-dioxaspiro[4.4]non-2-yl}ethoxy)dimethylsilane 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:

(2R,3R)-[3-(4'-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanol (607358-63-4) → tert-butyl(2-{(2S,3S)-3-[1-((2R,3R)-3-{[(4-methoxybenzyl)oxy]methyl}-1,4-dioxaspiro[4.4]non-2-yl)vinyl]-1,4-dioxaspiro[4.4]non-2-yl}ethoxy)dimethylsilane (692734-54-6)

Guidance literature:

Multi-step reaction with 7 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

7.1: NaHMDS / tetrahydrofuran / 0 - 20 °C

7.2: 6.351 g / tetrahydrofuran / 11 h / 0 °C

With potassium osmate(VI); n-butyllithium; oxalyl dichloride; (DHQ)2-PHAL; sodium hexamethyldisilazane; 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 / 7.2: Wittig reaction;

DOI:10.1021/ja0533646

Reference yield:

(2S,3R)-3-(4-Methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]nonane-2-carbaldehyde (692734-63-7) → tert-butyl(2-{(2S,3S)-3-[1-((2R,3R)-3-{[(4-methoxybenzyl)oxy]methyl}-1,4-dioxaspiro[4.4]non-2-yl)vinyl]-1,4-dioxaspiro[4.4]non-2-yl}ethoxy)dimethylsilane (692734-54-6)

Guidance literature:

Multi-step reaction with 6 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

6.1: NaHMDS / tetrahydrofuran / 0 - 20 °C

6.2: 6.351 g / tetrahydrofuran / 11 h / 0 °C

With potassium osmate(VI); n-butyllithium; (DHQ)2-PHAL; sodium hexamethyldisilazane; 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 / 6.2: Wittig reaction;

DOI:10.1021/ja0533646

Reference yield:

(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 (692734-53-5) → tert-butyl(2-{(2S,3S)-3-[1-((2R,3R)-3-{[(4-methoxybenzyl)oxy]methyl}-1,4-dioxaspiro[4.4]non-2-yl)vinyl]-1,4-dioxaspiro[4.4]non-2-yl}ethoxy)dimethylsilane (692734-54-6)

Guidance literature:

Multi-step reaction with 3 steps

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

2.1: TsOH*H₂O / CH₂Cl₂ / 2 h / 0 °C

3.1: NaHMDS / tetrahydrofuran / 0 - 20 °C

3.2: 6.351 g / tetrahydrofuran / 11 h / 0 °C

With potassium osmate(VI); (DHQ)2-PHAL; sodium hexamethyldisilazane; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); methanesulfonamide; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation / 3.2: Wittig reaction;

DOI:10.1021/ja0533646

upstream raw materials:

Methyltriphenylphosphonium bromide

{(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

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

5-(tert-Butyl-dimethyl-silanyloxy)-1-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-pent-2-yn-1-ol

Downstream raw materials:

((2S,3S)-3-{1-[(2R,3R)-3-(4-Methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-vinyl}-1,4-dioxa-spiro[4.4]non-2-yl)-acetaldehyde

C₂₈H₃₈O₆

(+)-amphidinolide A

2-((2S,3S)-3-{1-[(2R,3R)-3-(4-Methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-vinyl}-1,4-dioxa-spiro[4.4]non-2-yl)-ethanol