(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

Base Information

• Chemical Name: (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
• CAS No.: 692734-53-5
• Molecular Formula: C₂₇H₄₂O₆Si
• Molecular Weight: 490.712
• Mol file: 692734-53-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 7 articles about (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 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: 86.0%

(E)-(R)-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 (692734-44-4) → (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)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ja049292k

Reference yield: 86.0%

(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 (868056-92-2) → (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)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃;

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) → (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)

Guidance literature:

Multi-step reaction with 4 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

With n-butyllithium; oxalyl dichloride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.1: Moffat-Swern oxidation;

DOI:10.1021/ja0533646

upstream raw materials:

(E)-(R)-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

(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

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

Downstream raw materials:

(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

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

((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