(3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrroline

Base Information

• Chemical Name: (3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrroline
• CAS No.: 872345-50-1
• Molecular Formula: C₅₂H₅₉NO₄Si₂
• Molecular Weight: 818.216

Synonyms:(3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrroline

Chemical Property of (3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrroline

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Technology Process of (3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrroline

There total 8 articles about (3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrroline 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: 97.0%

5-azido-3,4-di-O-benzyl-1,6-di-O-tert-butyldiphenylsilyl-5-deoxy-D-psicose (872345-48-7) → (3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ2-pyrroline (872345-50-1)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; for 5h; Heating;

DOI:10.1016/j.tet.2005.09.043

Reference yield:

(5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one (872345-44-3) → (3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ2-pyrroline (872345-50-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88 percent / NaBH₄ / methanol / 1 h / cooling

2.1: 72 percent / NaH / dimethylformamide / 2 h / 20 °C

3.1: aq. TFA / 2 h / 20 °C

3.2: 2.31 g / imidazole / dimethylformamide / 20 h / 20 °C

4.1: 97 percent / PPh₃ / tetrahydrofuran / 5 h / Heating

With sodium tetrahydroborate; sodium hydride; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 4.1: Staudinger/aza-Wittig reaction;

DOI:10.1016/j.tet.2005.09.043

Reference yield:

5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose (872345-45-4) → (3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ2-pyrroline (872345-50-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 72 percent / NaH / dimethylformamide / 2 h / 20 °C

2.1: aq. TFA / 2 h / 20 °C

2.2: 2.31 g / imidazole / dimethylformamide / 20 h / 20 °C

3.1: 97 percent / PPh₃ / tetrahydrofuran / 5 h / Heating

With sodium hydride; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; N,N-dimethyl-formamide; 3.1: Staudinger/aza-Wittig reaction;

DOI:10.1016/j.tet.2005.09.043

upstream raw materials:

5-azido-3,4-di-O-benzyl-1,6-di-O-tert-butyldiphenylsilyl-5-deoxy-D-psicose

(5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one

5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose

5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose

Downstream raw materials:

(2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrrolidine

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