Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester

Base Information

• Chemical Name: Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester
• CAS No.: 544686-92-2
• Molecular Formula: C₆₁H₇₇N₂O₉PSi
• Molecular Weight: 1041.35

Synonyms:Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester

Chemical Property of Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester

Chemical Property:

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Technology Process of Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester

There total 11 articles about Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl 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: 85.0%

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite (108549-21-9) + 2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol (544686-91-1) → Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester (544686-92-2)

Guidance literature:

In dichloromethane;

DOI:10.1002/anie.200390243

Reference yield:

(S)-(-)-1-allyl-3-tert-butyldiphenylsilyl-sn-glycerol (544686-87-5) → Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester (544686-92-2)

Guidance literature:

Multi-step reaction with 8 steps

1: TMSOTf / CH₂Cl₂ / 0.03 h / 20 °C

2: MeOH; NaOMe / pH 9

3: 8.17 g / sodium hydride / dimethylformamide / 24 h / 20 °C

4: 1,3-propanedithiol; Et₃N / pyridine; H₂O

5: 5.82 g / pyridine / 2 h

6: DBU / (Ph₃P)3RhCl / ethanol / 0.25 h / 90 °C

7: 1.98 g / aqueous HCl / acetone / 0.25 h / 70 °C

8: 85 percent / tetrazole / CH₂Cl₂ / 0.25 h / 20 °C

With pyridine; 1H-tetrazole; 1.3-propanedithiol; hydrogenchloride; methanol; sodium methylate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; Wilkinson's catalyst; trimethylsilyl trifluoromethanesulfonate; In pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tetasy.2004.11.070

Reference yield:

(2R,3S,4R,5R,6S)-6-[(S)-1-Allyloxymethyl-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-5-azido-2-hydroxymethyl-tetrahydro-pyran-3,4-diol → Diisopropyl-phosphoramidous acid (R)-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester benzyl ester (544686-92-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 8.17 g / sodium hydride / dimethylformamide / 24 h / 20 °C

2: 1,3-propanedithiol; Et₃N / pyridine; H₂O

3: 5.82 g / pyridine / 2 h

4: DBU / (Ph₃P)3RhCl / ethanol / 0.25 h / 90 °C

5: 1.98 g / aqueous HCl / acetone / 0.25 h / 70 °C

6: 85 percent / tetrazole / CH₂Cl₂ / 0.25 h / 20 °C

With pyridine; 1H-tetrazole; 1.3-propanedithiol; hydrogenchloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; Wilkinson's catalyst; In pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tetasy.2004.11.070

upstream raw materials:

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite

2-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-1-O-tert-butyldiphenylsilyl-sn-glycerol

benzyl bromide

(S)-(-)-1-allyl-3-tert-butyldiphenylsilyl-sn-glycerol

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