(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

Base Information

Chemical Name:(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
CAS No.:692734-44-4
Molecular Formula:C₂₇H₄₄O₆Si
Molecular Weight:492.728
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 4 articles about (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 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:

: 692734-64-8
(R)-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

: 692734-44-4
(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

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; toluene; at 20 ℃; for 6h;
DOI:10.1021/ja049292k

Reference yield:

: 78592-82-2
4-(tert-butyldimethylsilyloxy)-1-butyne

: 692734-44-4
(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

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: 2.636 g / Red-Al(R) / tetrahydrofuran; toluene / 6 h / 20 °C

With n-butyllithium; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; toluene;
DOI:10.1021/ja049292k

Reference yield:

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

: 692734-44-4
(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

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: 2.636 g / Red-Al(R) / tetrahydrofuran; toluene / 6 h / 20 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.1: Swern oxidation;
DOI:10.1021/ja049292k