(1R,2S,3S,4S,5R)-1-formyloxy-2-benzyloxy-3,4-O-isopropylidene-5-iodomethyl-1,2,3,4-cyclopentane-tetrol

Base Information

Chemical Name:(1R,2S,3S,4S,5R)-1-formyloxy-2-benzyloxy-3,4-O-isopropylidene-5-iodomethyl-1,2,3,4-cyclopentane-tetrol
CAS No.:855517-40-7
Molecular Formula:C₁₇H₂₁IO₅
Molecular Weight:432.255
Hs Code.:

Synonyms:(1R,2S,3S,4S,5R)-1-formyloxy-2-benzyloxy-3,4-O-isopropylidene-5-iodomethyl-1,2,3,4-cyclopentane-tetrol

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Chemical Property of (1R,2S,3S,4S,5R)-1-formyloxy-2-benzyloxy-3,4-O-isopropylidene-5-iodomethyl-1,2,3,4-cyclopentane-tetrol

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Technology Process of (1R,2S,3S,4S,5R)-1-formyloxy-2-benzyloxy-3,4-O-isopropylidene-5-iodomethyl-1,2,3,4-cyclopentane-tetrol

There total 6 articles about (1R,2S,3S,4S,5R)-1-formyloxy-2-benzyloxy-3,4-O-isopropylidene-5-iodomethyl-1,2,3,4-cyclopentane-tetrol 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: 62.0%

: 855517-39-4
(1R,5S,6S,7S,8S)-8-benzyloxy-6,7-isopropylidenedioxy-2-oxabicyclo[3.3.0]oct-3-ol

: 855517-40-7
(1R,2S,3S,4S,5R)-1-formyloxy-2-benzyloxy-3,4-O-isopropylidene-5-iodomethyl-1,2,3,4-cyclopentane-tetrol

Guidance literature:: With [bis(acetoxy)iodo]benzene; iodine; In cyclohexane; at 25 ℃; for 0.666667h; Irradiation;
DOI:10.1039/b501824b

Reference yield:

: 855517-37-2
(1R,5R,8R)-8-benzyloxy-2-oxabicyclo[3.3.0]oct-6-en-3-one

: 855517-40-7
(1R,2S,3S,4S,5R)-1-formyloxy-2-benzyloxy-3,4-O-isopropylidene-5-iodomethyl-1,2,3,4-cyclopentane-tetrol

Guidance literature:: Multi-step reaction with 4 steps

1: OsO₄; NMO*H₂O / CH₂Cl₂ / 25 °C

2: 180 mg / H₂SO₄ / acetone / 0.5 h / 25 °C

3: 88 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

4: 62 percent / (diacetoxyiodo)benzene; I₂ / cyclohexane / 0.67 h / 25 °C / Irradiation

With osmium(VIII) oxide; [bis(acetoxy)iodo]benzene; sulfuric acid; iodine; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In dichloromethane; cyclohexane; acetone;
DOI:10.1039/b501824b

Reference yield:

: (3aR,6R,6aR)-6-Benzyloxy-4,5-dihydroxy-hexahydro-cyclopenta[b]furan-2-one

: 855517-40-7
(1R,2S,3S,4S,5R)-1-formyloxy-2-benzyloxy-3,4-O-isopropylidene-5-iodomethyl-1,2,3,4-cyclopentane-tetrol

Guidance literature:: Multi-step reaction with 3 steps

1: 180 mg / H₂SO₄ / acetone / 0.5 h / 25 °C

2: 88 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

3: 62 percent / (diacetoxyiodo)benzene; I₂ / cyclohexane / 0.67 h / 25 °C / Irradiation

With [bis(acetoxy)iodo]benzene; sulfuric acid; iodine; diisobutylaluminium hydride; In dichloromethane; cyclohexane; acetone;
DOI:10.1039/b501824b