((5S,7S,8R,9R)-9-Benzyloxy-8-hydroxy-2,2-dimethyl-1,3-dioxa-spiro[4.5]dec-7-ylmethyl)-phosphonic acid diisopropyl ester

Base Information

Chemical Name:((5S,7S,8R,9R)-9-Benzyloxy-8-hydroxy-2,2-dimethyl-1,3-dioxa-spiro[4.5]dec-7-ylmethyl)-phosphonic acid diisopropyl ester
CAS No.:135525-92-7
Molecular Formula:C₂₄H₃₉O₇P
Molecular Weight:470.543
Hs Code.:

Synonyms:((5S,7S,8R,9R)-9-Benzyloxy-8-hydroxy-2,2-dimethyl-1,3-dioxa-spiro[4.5]dec-7-ylmethyl)-phosphonic acid diisopropyl ester

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Chemical Property of ((5S,7S,8R,9R)-9-Benzyloxy-8-hydroxy-2,2-dimethyl-1,3-dioxa-spiro[4.5]dec-7-ylmethyl)-phosphonic acid diisopropyl ester

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Technology Process of ((5S,7S,8R,9R)-9-Benzyloxy-8-hydroxy-2,2-dimethyl-1,3-dioxa-spiro[4.5]dec-7-ylmethyl)-phosphonic acid diisopropyl ester

There total 8 articles about ((5S,7S,8R,9R)-9-Benzyloxy-8-hydroxy-2,2-dimethyl-1,3-dioxa-spiro[4.5]dec-7-ylmethyl)-phosphonic acid diisopropyl ester 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: 79.0%

: 141269-66-1
C₁₇H₂₂O₄

: 135525-92-7
((5S,7S,8R,9R)-9-Benzyloxy-8-hydroxy-2,2-dimethyl-1,3-dioxa-spiro[4.5]dec-7-ylmethyl)-phosphonic acid diisopropyl ester

Guidance literature:: In tetrahydrofuran; at -78 ℃;
DOI:10.1021/ja00016a070

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 135525-92-7
((5S,7S,8R,9R)-9-Benzyloxy-8-hydroxy-2,2-dimethyl-1,3-dioxa-spiro[4.5]dec-7-ylmethyl)-phosphonic acid diisopropyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / p-TsOH / benzene / Heating

2: 76 percent / NaBH₄ / ethanol / 0 °C

3: 79 percent / p-TsOH / dimethylformamide / Ambient temperature

4: 79 percent / NBS / benzene / Ambient temperature

5: 87 percent / MeONa / methanol; tetrahydrofuran / 0 °C

6: 96 percent / NaH, n-Bu₄NI / tetrahydrofuran / 0 °C

7: 79 percent / tetrahydrofuran / -78 °C

With sodium tetrahydroborate; N-Bromosuccinimide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00016a070

Reference yield:

: 100-39-0
benzyl bromide

: 135525-92-7
((5S,7S,8R,9R)-9-Benzyloxy-8-hydroxy-2,2-dimethyl-1,3-dioxa-spiro[4.5]dec-7-ylmethyl)-phosphonic acid diisopropyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / NaH, n-Bu₄NI / tetrahydrofuran / 0 °C

2: 79 percent / tetrahydrofuran / -78 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;
DOI:10.1021/ja00016a070