2,5-anhydro-1-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-5-C-mesyloxymethyl-6-O-mesyl-D-allitol

Base Information

Chemical Name:2,5-anhydro-1-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-5-C-mesyloxymethyl-6-O-mesyl-D-allitol
CAS No.:561018-00-6
Molecular Formula:C₂₈H₄₀O₁₀S₂Si
Molecular Weight:628.837
Hs Code.:

Synonyms:2,5-anhydro-1-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-5-C-mesyloxymethyl-6-O-mesyl-D-allitol

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Chemical Property of 2,5-anhydro-1-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-5-C-mesyloxymethyl-6-O-mesyl-D-allitol

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Technology Process of 2,5-anhydro-1-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-5-C-mesyloxymethyl-6-O-mesyl-D-allitol

There total 9 articles about 2,5-anhydro-1-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-5-C-mesyloxymethyl-6-O-mesyl-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: 93.0%

: 124-63-0
methanesulfonyl chloride

: 561017-98-9
2,5-anhydro-1-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-5-C-hydroxymethyl-D-allitol

: 561018-00-6
2,5-anhydro-1-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-5-C-mesyloxymethyl-6-O-mesyl-D-allitol

Guidance literature:: In pyridine; at 20 ℃; for 16h;
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

: 561018-00-6
2,5-anhydro-1-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-5-C-mesyloxymethyl-6-O-mesyl-D-allitol

Guidance literature:: Multi-step reaction with 8 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

With sodium hydroxide; dicobalt octacarbonyl; potassium tert-butylate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; acetone; 7.2: Cannizaro reduction;
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

: 561018-00-6
2,5-anhydro-1-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-5-C-mesyloxymethyl-6-O-mesyl-D-allitol

Guidance literature:: Multi-step reaction with 7 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

With sodium hydroxide; potassium tert-butylate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; acetone; 6.2: Cannizaro reduction;
DOI:10.1016/S0040-4020(03)00288-6