D-Tryptophan, N-[(phenylmethoxy)carbonyl]-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-

Base Information

Chemical Name:D-Tryptophan, N-[(phenylmethoxy)carbonyl]-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-
CAS No.:872877-20-8
Molecular Formula:C25H29BN2O6
Molecular Weight:464.326
Hs Code.:

Synonyms:

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Chemical Property of D-Tryptophan, N-[(phenylmethoxy)carbonyl]-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-

Chemical Property:

Purity/Quality:

Safty Information:

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Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of D-Tryptophan, N-[(phenylmethoxy)carbonyl]-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-

There total 11 articles about D-Tryptophan, N-[(phenylmethoxy)carbonyl]-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)- 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: 100.0%

: 872877-18-4
(R)-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-N-carbobenzyloxy-6'-iodotryptophan tert-butyl ester

: 872877-20-8
(R)-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-N-carbobenzyloxytryptophan

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 3.5h;
DOI:10.1248/cpb.53.1277

Reference yield:

: 19727-83-4
6-nitroindoline

: 872877-20-8
(R)-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-N-carbobenzyloxytryptophan

Guidance literature:: Multi-step reaction with 11 steps

1: 96 percent / pyridine / 1.4 h / 20 °C

2: 100 percent / H₂ / Pd/C / methanol / 1.4 h / 20 °C

3: 62 percent / aq. NaNO₂; AcOH; KI / 24 h / 0 °C

4: 71 percent / aq. NaOH / methanol / 4.5 h / 75 °C

5: 98 percent / salcomine; O₂ / methanol / 3.5 h / 20 °C

6: 89 percent / AcOH / 2 h / 75 °C

7: 48.3 percent / D-aminocyclase; aq. phosphate buffer; CoCl₂ / 47 h / 37 °C / pH 7.4

8: 100 percent / aq. Na₂CO₃ / diethyl ether / 3 h / 0 °C

9: 82 percent / K₂CO₃; benzyltriethylammonium chloride / N,N-dimethyl-acetamide / 2.5 h / 55 °C

10: 36.6 percent / Pd(dppf)Cl₂; KOAc / dimethylsulfoxide / 3 h / 77 °C

11: 100 percent / TFA / CH₂Cl₂ / 3.5 h / 0 °C

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide; phosphate buffer; D-aminocyclase; salcomine; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; oxygen; potassium acetate; sodium carbonate; potassium carbonate; acetic acid; trifluoroacetic acid; potassium iodide; sodium nitrite; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; N,N-dimethyl acetamide; dimethyl sulfoxide;
DOI:10.1248/cpb.53.1277

Reference yield:

: 22949-08-2
1-acetyl-6-nitro-2,3-dihydroindole

: 872877-20-8
(R)-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-N-carbobenzyloxytryptophan

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / H₂ / Pd/C / methanol / 1.4 h / 20 °C

2: 62 percent / aq. NaNO₂; AcOH; KI / 24 h / 0 °C

3: 71 percent / aq. NaOH / methanol / 4.5 h / 75 °C

4: 98 percent / salcomine; O₂ / methanol / 3.5 h / 20 °C

5: 89 percent / AcOH / 2 h / 75 °C

6: 48.3 percent / D-aminocyclase; aq. phosphate buffer; CoCl₂ / 47 h / 37 °C / pH 7.4

7: 100 percent / aq. Na₂CO₃ / diethyl ether / 3 h / 0 °C

8: 82 percent / K₂CO₃; benzyltriethylammonium chloride / N,N-dimethyl-acetamide / 2.5 h / 55 °C

9: 36.6 percent / Pd(dppf)Cl₂; KOAc / dimethylsulfoxide / 3 h / 77 °C

10: 100 percent / TFA / CH₂Cl₂ / 3.5 h / 0 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide; phosphate buffer; D-aminocyclase; salcomine; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; oxygen; potassium acetate; sodium carbonate; potassium carbonate; acetic acid; trifluoroacetic acid; potassium iodide; sodium nitrite; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; N,N-dimethyl acetamide; dimethyl sulfoxide;
DOI:10.1248/cpb.53.1277