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

Base Information

Chemical Name:((1S,2R,3R,5R)-3-Benzyloxy-2,5-dihydroxy-5-hydroxymethyl-cyclohexylmethyl)-phosphonic acid diisopropyl ester
CAS No.:141171-62-2
Molecular Formula:C₂₁H₃₅O₇P
Molecular Weight:430.478
Hs Code.:

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

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

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

There total 11 articles about ((1S,2R,3R,5R)-3-Benzyloxy-2,5-dihydroxy-5-hydroxymethyl-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: 93.0%

: 141269-65-0
<5R-(5α,7α,8β,9α)>-7-(benzyloxy)-2,2-dimethyl-9-<(diisopropoxyphosphinyl)methyl>-1,3-dioxaspiro<4.5>decan-8-ol

: 141171-62-2
((1S,2R,3R,5R)-3-Benzyloxy-2,5-dihydroxy-5-hydroxymethyl-cyclohexylmethyl)-phosphonic acid diisopropyl ester

Guidance literature:: With acetic acid; In tetrahydrofuran; at 65 - 75 ℃; for 5h;
DOI:10.1021/ja00038a002

Reference yield:

: 1445-75-6
diisopropyl methanephosphonate

: 141171-62-2
((1S,2R,3R,5R)-3-Benzyloxy-2,5-dihydroxy-5-hydroxymethyl-cyclohexylmethyl)-phosphonic acid diisopropyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) n-butyllithium, 2.) boron trifluoride etherate

2: 93 percent / 50percent aq. acetic acid / tetrahydrofuran / 5 h / 65 - 75 °C

With n-butyllithium; boron trifluoride diethyl etherate; acetic acid; In tetrahydrofuran;
DOI:10.1021/ja00038a002

Reference yield:

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

: 141171-62-2
((1S,2R,3R,5R)-3-Benzyloxy-2,5-dihydroxy-5-hydroxymethyl-cyclohexylmethyl)-phosphonic acid diisopropyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent / p-toluenesulfonic acid (p-TsOH) / benzene / Heating

2: 75 percent / NaBH₄ / ethanol / 0.75 h / 0 °C

3: 70 percent / p-toluenesulfonic acid (p-TsOH) / dimethylformamide / 24 h / Ambient temperature

4: 79 percent / N-bromosuccinimide (NBS) / benzene / Heating

5: 11 percent / MeONa / tetrahydrofuran; methanol / 0.5 h / Heating

6: 1.) NaH / 1.) THF, hexane, 30 min, 2.) THF, hexane, RT, 12 h

7: 1.) n-butyllithium, 2.) boron trifluoride etherate

8: 93 percent / 50percent aq. acetic acid / tetrahydrofuran / 5 h / 65 - 75 °C

With sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00038a002