((1S,3R,5S)-3-Benzyloxy-5-hydroxy-5-hydroxymethyl-2-oxo-cyclohexylmethyl)-phosphonic acid diisopropyl ester

Base Information

Chemical Name:((1S,3R,5S)-3-Benzyloxy-5-hydroxy-5-hydroxymethyl-2-oxo-cyclohexylmethyl)-phosphonic acid diisopropyl ester
CAS No.:135525-93-8
Molecular Formula:C₂₁H₃₃O₇P
Molecular Weight:428.463
Hs Code.:

Synonyms:((1S,3R,5S)-3-Benzyloxy-5-hydroxy-5-hydroxymethyl-2-oxo-cyclohexylmethyl)-phosphonic acid diisopropyl ester

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Chemical Property of ((1S,3R,5S)-3-Benzyloxy-5-hydroxy-5-hydroxymethyl-2-oxo-cyclohexylmethyl)-phosphonic acid diisopropyl ester

Chemical Property:

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Technology Process of ((1S,3R,5S)-3-Benzyloxy-5-hydroxy-5-hydroxymethyl-2-oxo-cyclohexylmethyl)-phosphonic acid diisopropyl ester

There total 10 articles about ((1S,3R,5S)-3-Benzyloxy-5-hydroxy-5-hydroxymethyl-2-oxo-cyclohexylmethyl)-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:

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

: 135525-93-8
((1S,3R,5S)-3-Benzyloxy-5-hydroxy-5-hydroxymethyl-2-oxo-cyclohexylmethyl)-phosphonic acid diisopropyl ester

Guidance literature:: With acetic acid; In tetrahydrofuran; water; at 65 ℃; Yield given;
DOI:10.1021/ja00016a070

Reference yield:

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

: 135525-93-8
((1S,3R,5S)-3-Benzyloxy-5-hydroxy-5-hydroxymethyl-2-oxo-cyclohexylmethyl)-phosphonic acid diisopropyl ester

Guidance literature:: Multi-step reaction with 9 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

8: 95 percent / (COCl)2, DMSO / CH₂Cl₂ / -78 °C

9: AcOH / H₂O; tetrahydrofuran / 65 °C

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

Reference yield:

: 100-39-0
benzyl bromide

: 135525-93-8
((1S,3R,5S)-3-Benzyloxy-5-hydroxy-5-hydroxymethyl-2-oxo-cyclohexylmethyl)-phosphonic acid diisopropyl ester

Guidance literature:: Multi-step reaction with 4 steps

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

2: 79 percent / tetrahydrofuran / -78 °C

3: 95 percent / (COCl)2, DMSO / CH₂Cl₂ / -78 °C

4: AcOH / H₂O; tetrahydrofuran / 65 °C

With oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ja00016a070