(2R,3S)-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

Base Information

• Chemical Name: (2R,3S)-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
• CAS No.: 868056-88-6
• Molecular Formula: C₂₇H₄₄O₈Si
• Molecular Weight: 524.727

Synonyms:(2R,3S)-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

Chemical Property of (2R,3S)-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

Chemical Property:

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Technology Process of (2R,3S)-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

There total 6 articles about (2R,3S)-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 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:

(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) → (2R,3S)-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 (868056-88-6)

Guidance literature:

With methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); potassium osmate(VI); (DHQ)2-PHAL; In tert-butyl alcohol; at 0 ℃; for 22h;

DOI:10.1021/ja049292k

Reference yield:

4-(tert-butyldimethylsilyloxy)-1-butyne (78592-82-2) → (2R,3S)-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 (868056-88-6)

Guidance literature:

Multi-step reaction with 4 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: 2.636 g / Red-Al(R) / tetrahydrofuran; toluene / 6 h / 20 °C

3.1: 86 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4.1: K₃Fe(CN)6; K₂CO₃; methanesulfonamide / (DHQ)2-PHAL; aq. K₂OsO₄ / 2-methyl-propan-2-ol / 22 h / 0 °C

With n-butyllithium; methanesulfonamide; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; sodium bis(2-methoxyethoxy)aluminium dihydride; potassium hexacyanoferrate(III); potassium osmate(VI); (DHQ)2-PHAL; In tetrahydrofuran; hexane; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1021/ja049292k

Reference yield:

(2R,3R)-[3-(4'-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-methanol (607358-63-4) → (2R,3S)-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 (868056-88-6)

Guidance literature:

Multi-step reaction with 5 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: 2.636 g / Red-Al(R) / tetrahydrofuran; toluene / 6 h / 20 °C

4.1: 86 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5.1: K₃Fe(CN)6; K₂CO₃; methanesulfonamide / (DHQ)2-PHAL; aq. K₂OsO₄ / 2-methyl-propan-2-ol / 22 h / 0 °C

With n-butyllithium; oxalyl dichloride; methanesulfonamide; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; potassium hexacyanoferrate(III); potassium osmate(VI); (DHQ)2-PHAL; In tetrahydrofuran; hexane; dichloromethane; toluene; tert-butyl alcohol; 1.1: Swern oxidation;

DOI:10.1021/ja049292k

upstream raw materials:

(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

4-(tert-butyldimethylsilyloxy)-1-butyne

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

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

Downstream raw materials:

{(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

(+)-amphidinolide A

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

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

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