((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
• Mol file: 141171-62-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

<5R-(5α,7α,8β,9α)>-7-(benzyloxy)-2,2-dimethyl-9-<(diisopropoxyphosphinyl)methyl>-1,3-dioxaspiro<4.5>decan-8-ol (141269-65-0) → ((1S,2R,3R,5R)-3-Benzyloxy-2,5-dihydroxy-5-hydroxymethyl-cyclohexylmethyl)-phosphonic acid diisopropyl ester (141171-62-2)

Guidance literature:

With acetic acid; In tetrahydrofuran; at 65 - 75 ℃; for 5h;

DOI:10.1021/ja00038a002

Reference yield:

diisopropyl methanephosphonate (1445-75-6) → ((1S,2R,3R,5R)-3-Benzyloxy-2,5-dihydroxy-5-hydroxymethyl-cyclohexylmethyl)-phosphonic acid diisopropyl ester (141171-62-2)

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:

D-(-)-quinic acid (77-95-2) → ((1S,2R,3R,5R)-3-Benzyloxy-2,5-dihydroxy-5-hydroxymethyl-cyclohexylmethyl)-phosphonic acid diisopropyl ester (141171-62-2)

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

upstream raw materials:

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

diisopropyl methanephosphonate

D-(-)-quinic acid

benzyl bromide

Downstream raw materials:

<1R-(1α,3α,4β,5α)>-1,3,4-trihydroxy-5-<(diisopropoxyphosphinyl)methyl>cyclohexan-1-carboxylic acid

<1R-(1α,3α,4β,5α)>-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid

<1R-(1α,3α,4β,5α)>-1-(hydroxymethyl)-5-<(diisopropoxyphosphinyl)methyl>cyclohexan-1,3,4-triol