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

Base Information

• Chemical Name: 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
• CAS No.: 692734-55-7
• Molecular Formula: C₂₇H₃₈O₇
• Molecular Weight: 474.595
• Mol file: 692734-55-7.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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: 78.0%

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) → 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 (692734-55-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/ja049292k DOI:10.1021/ja0533646

Reference yield:

(2R,3R)-[3-(4'-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanol (607358-63-4) → 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 (692734-55-7)

Guidance literature:

Multi-step reaction with 8 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

8.1: 78 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

With potassium osmate(VI); n-butyllithium; oxalyl dichloride; (DHQ)2-PHAL; tetrabutyl ammonium fluoride; 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) → 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 (692734-55-7)

Guidance literature:

Multi-step reaction with 7 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

7.1: 78 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

With potassium osmate(VI); n-butyllithium; (DHQ)2-PHAL; tetrabutyl ammonium fluoride; 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

upstream raw materials:

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

(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

5-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-1-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-pentan-1-one

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