2,2-Dimethyl-propionic acid (2S,3S,4S,5R)-4,5-bis-benzyloxy-2-iodomethyl-6-oxo-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2S,3S,4S,5R)-4,5-bis-benzyloxy-2-iodomethyl-6-oxo-tetrahydro-pyran-3-yl ester
CAS No.:440339-68-4
Molecular Formula:C₂₅H₂₉IO₆
Molecular Weight:552.406
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (2S,3S,4S,5R)-4,5-bis-benzyloxy-2-iodomethyl-6-oxo-tetrahydro-pyran-3-yl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2S,3S,4S,5R)-4,5-bis-benzyloxy-2-iodomethyl-6-oxo-tetrahydro-pyran-3-yl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2S,3S,4S,5R)-4,5-bis-benzyloxy-2-iodomethyl-6-oxo-tetrahydro-pyran-3-yl ester

There total 6 articles about 2,2-Dimethyl-propionic acid (2S,3S,4S,5R)-4,5-bis-benzyloxy-2-iodomethyl-6-oxo-tetrahydro-pyran-3-yl 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:

: 2,2-Dimethyl-propionic acid (2S,3S,4S,5R,6S)-4,5-bis-benzyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yl ester

: 440339-68-4
2,2-Dimethyl-propionic acid (2S,3S,4S,5R)-4,5-bis-benzyloxy-2-iodomethyl-6-oxo-tetrahydro-pyran-3-yl ester

Guidance literature:: 2,2-Dimethyl-propionic acid (2S,3S,4S,5R,6S)-4,5-bis-benzyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yl ester; With sulfuric acid; acetic anhydride; at -5 - 0 ℃; for 0.25h;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 168h;

With acetic anhydride; In dimethyl sulfoxide; at 20 ℃; for 12h;
DOI:10.1016/S0040-4020(02)00044-3

Reference yield:

: 76491-08-2
methyl 2,3-di-O-benzyl-4,6-O-isopropylidene-α-D-glucopyranoside

: 440339-68-4
2,2-Dimethyl-propionic acid (2S,3S,4S,5R)-4,5-bis-benzyloxy-2-iodomethyl-6-oxo-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 117 g / Amberlyst-15E / methanol / 18 h / 20 °C

2.1: 85 percent / imidazole; PPh₃; I₂ / toluene / 2 h / 20 °C

3.1: DMAP / CH₂Cl₂ / 48 h / 20 °C

4.1: Ac₂O; aq. H₂SO₄ / 0.25 h / -5 - 0 °C

4.2: aq. HCl / tetrahydrofuran / 168 h / 20 °C

4.3: 61.0 g / Ac₂O / dimethylsulfoxide / 12 h / 20 °C

With 1H-imidazole; dmap; Amberlyst-15E; sulfuric acid; iodine; acetic anhydride; triphenylphosphine; In methanol; dichloromethane; toluene;
DOI:10.1016/S0040-4020(02)00044-3

Reference yield:

: 87326-88-3
methyl 6-deoxy-6-iodo-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside

: 440339-68-4
2,2-Dimethyl-propionic acid (2S,3S,4S,5R)-4,5-bis-benzyloxy-2-iodomethyl-6-oxo-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: DMAP / CH₂Cl₂ / 48 h / 20 °C

2.1: Ac₂O; aq. H₂SO₄ / 0.25 h / -5 - 0 °C

2.2: aq. HCl / tetrahydrofuran / 168 h / 20 °C

2.3: 61.0 g / Ac₂O / dimethylsulfoxide / 12 h / 20 °C

With dmap; sulfuric acid; acetic anhydride; In dichloromethane;
DOI:10.1016/S0040-4020(02)00044-3