(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

Base Information

• Chemical Name: (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
• CAS No.: 868056-92-2
• Molecular Formula: C₂₇H₄₄O₆Si
• Molecular Weight: 492.728
• Mol file: 868056-92-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 3 articles about (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 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:

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 (868056-85-3) → (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)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; toluene; 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-[(2R,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-pent-2-en-1-ol (868056-92-2)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/ja0533646

Reference yield:

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

Guidance literature:

Multi-step reaction with 2 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

With n-butyllithium; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; toluene;

DOI:10.1021/ja0533646

upstream raw materials:

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

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

Downstream 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

{(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

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

C₂₈H₃₈O₆