2,5-anhydro-6-tert-butoxycarbonylamino-1-O-tert-butyldiphenylsilyl-6-deoxy-4-O,5-C-methylene-D-allitol

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Chemical Name:2,5-anhydro-6-tert-butoxycarbonylamino-1-O-tert-butyldiphenylsilyl-6-deoxy-4-O,5-C-methylene-D-allitol
CAS No.:561018-08-4
Molecular Formula:C₂₈H₃₉NO₆Si
Molecular Weight:513.706
Hs Code.:

Synonyms:2,5-anhydro-6-tert-butoxycarbonylamino-1-O-tert-butyldiphenylsilyl-6-deoxy-4-O,5-C-methylene-D-allitol

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Chemical Property of 2,5-anhydro-6-tert-butoxycarbonylamino-1-O-tert-butyldiphenylsilyl-6-deoxy-4-O,5-C-methylene-D-allitol

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Technology Process of 2,5-anhydro-6-tert-butoxycarbonylamino-1-O-tert-butyldiphenylsilyl-6-deoxy-4-O,5-C-methylene-D-allitol

There total 13 articles about 2,5-anhydro-6-tert-butoxycarbonylamino-1-O-tert-butyldiphenylsilyl-6-deoxy-4-O,5-C-methylene-D-allitol 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: 94.0%

: 58632-95-4
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

: 561018-06-2
2,5-anhydro-6-azido-1-O-tert-butyldiphenylsilyl-6-deoxy-4-O,5-C-methylene-D-allitol

: 561018-08-4
2,5-anhydro-6-tert-butoxycarbonylamino-1-O-tert-butyldiphenylsilyl-6-deoxy-4-O,5-C-methylene-D-allitol

Guidance literature:: With trimethylphosphane; In tetrahydrofuran; toluene; at -20 ℃; for 5h;
DOI:10.1016/S0040-4020(03)00288-6

Reference yield:

: 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 561018-08-4
2,5-anhydro-6-tert-butoxycarbonylamino-1-O-tert-butyldiphenylsilyl-6-deoxy-4-O,5-C-methylene-D-allitol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 75 percent / Co₂(CO)8 / CH₂Cl₂ / 16 h / 30 °C

2.1: 95 percent / AcOH / H₂O; tetrahydrofuran / 2 h / 20 °C

3.1: 89 percent / pyridine / 16 h / 20 °C

4.1: 100 percent / t-BuOK / methanol / 2 h / 20 °C

5.1: 94 percent / p-TsOH / acetone / 3 h / 20 °C

6.1: Dess-Martin periodinate / CH₂Cl₂ / 1 h / 0 °C

7.1: 2N aq. NaOH / H₂O; dioxane / 1 h / 0 °C

7.2: 1.14 g / NaBH₄ / H₂O; dioxane / 2 h / 0 °C

8.1: 93 percent / pyridine / 16 h / 20 °C

9.1: 53 percent / FeCl₃ / CH₂Cl₂; methanol / 1.5 h / 20 °C

10.1: 85 percent / 1M NaOH / H₂O; dioxane / 1 h / 25 °C

11.1: 95 percent / NaN₃ / dimethylformamide / 2 h / 20 °C

12.1: 94 percent / Me₃P / tetrahydrofuran; toluene / 5 h / -20 °C

With sodium hydroxide; sodium azide; dicobalt octacarbonyl; potassium tert-butylate; iron(III) chloride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 7.2: Cannizaro reduction / 12.1: Staudinger reaction;
DOI:10.1016/S0040-4020(03)00288-6

Reference yield:

: 115141-23-6
1-deoxy-1-diethylmethylsilyloxymethyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

: 561018-08-4
2,5-anhydro-6-tert-butoxycarbonylamino-1-O-tert-butyldiphenylsilyl-6-deoxy-4-O,5-C-methylene-D-allitol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 95 percent / AcOH / H₂O; tetrahydrofuran / 2 h / 20 °C

2.1: 89 percent / pyridine / 16 h / 20 °C

3.1: 100 percent / t-BuOK / methanol / 2 h / 20 °C

4.1: 94 percent / p-TsOH / acetone / 3 h / 20 °C

5.1: Dess-Martin periodinate / CH₂Cl₂ / 1 h / 0 °C

6.1: 2N aq. NaOH / H₂O; dioxane / 1 h / 0 °C

6.2: 1.14 g / NaBH₄ / H₂O; dioxane / 2 h / 0 °C

7.1: 93 percent / pyridine / 16 h / 20 °C

8.1: 53 percent / FeCl₃ / CH₂Cl₂; methanol / 1.5 h / 20 °C

9.1: 85 percent / 1M NaOH / H₂O; dioxane / 1 h / 25 °C

10.1: 95 percent / NaN₃ / dimethylformamide / 2 h / 20 °C

11.1: 94 percent / Me₃P / tetrahydrofuran; toluene / 5 h / -20 °C

With sodium hydroxide; sodium azide; potassium tert-butylate; iron(III) chloride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 6.2: Cannizaro reduction / 11.1: Staudinger reaction;
DOI:10.1016/S0040-4020(03)00288-6