(2S,3S,4S,5S,6S)-3,4,5-Tris-benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-6-iodomethyl-2-methoxy-tetrahydro-pyran

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Chemical Name:(2S,3S,4S,5S,6S)-3,4,5-Tris-benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-6-iodomethyl-2-methoxy-tetrahydro-pyran
CAS No.:304671-94-1
Molecular Formula:C₃₄H₄₁IO₇
Molecular Weight:688.6
Hs Code.:

Synonyms:(2S,3S,4S,5S,6S)-3,4,5-Tris-benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-6-iodomethyl-2-methoxy-tetrahydro-pyran

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Chemical Property of (2S,3S,4S,5S,6S)-3,4,5-Tris-benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-6-iodomethyl-2-methoxy-tetrahydro-pyran

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Technology Process of (2S,3S,4S,5S,6S)-3,4,5-Tris-benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-6-iodomethyl-2-methoxy-tetrahydro-pyran

There total 7 articles about (2S,3S,4S,5S,6S)-3,4,5-Tris-benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-6-iodomethyl-2-methoxy-tetrahydro-pyran 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:

: 77-76-9
2,2-dimethoxy-propane

: 304671-87-2
(2S,3S,4S,5S,6S)-3-Allyl-3,4,5-tris-benzyloxy-6-iodomethyl-2-methoxy-tetrahydro-pyran

: (2S,3S,4S,5S,6S)-3,4,5-Tris-benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-6-iodomethyl-2-methoxy-tetrahydro-pyran

: 304671-94-1
(2S,3S,4S,5S,6S)-3,4,5-Tris-benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-6-iodomethyl-2-methoxy-tetrahydro-pyran

Guidance literature:: (2S,3S,4S,5S,6S)-3-Allyl-3,4,5-tris-benzyloxy-6-iodomethyl-2-methoxy-tetrahydro-pyran; With AD-mix-α; In water; tert-butyl alcohol; at 0 ℃; for 24h;

2,2-dimethoxy-propane; With toluene-4-sulfonic acid; In dichloromethane; for 0.5h;
DOI:10.3987/com-00-8987

Reference yield:

: 100-39-0
benzyl bromide

: 304671-94-1
(2S,3S,4S,5S,6S)-3,4,5-Tris-benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-6-iodomethyl-2-methoxy-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / NaH; n-Bu₄NI / dimethylformamide / 0 - 20 °C

2.1: 90 percent / LiAlH₄; AlCl₃ / diethyl ether / 0.25 h

3.1: 95 percent / I₂; PPh₃; imidazole / toluene / 2 h / Heating

4.1: AD-MIX-α / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

4.2: p-TsOH / CH₂Cl₂ / 0.5 h

With 1H-imidazole; AD-mix-α; lithium aluminium tetrahydride; aluminium trichloride; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; triphenylphosphine; In diethyl ether; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.3987/com-00-8987

Reference yield:

: 130983-50-5
methyl 3-O-benzyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose

: 304671-94-1
(2S,3S,4S,5S,6S)-3,4,5-Tris-benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-6-iodomethyl-2-methoxy-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 5 steps

1.1: diethyl ether; CH₂Cl₂ / -78 °C

2.1: 97 percent / NaH; n-Bu₄NI / dimethylformamide / 0 - 20 °C

3.1: 90 percent / LiAlH₄; AlCl₃ / diethyl ether / 0.25 h

4.1: 95 percent / I₂; PPh₃; imidazole / toluene / 2 h / Heating

5.1: AD-MIX-α / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

5.2: p-TsOH / CH₂Cl₂ / 0.5 h

With 1H-imidazole; AD-mix-α; lithium aluminium tetrahydride; aluminium trichloride; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; triphenylphosphine; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.3987/com-00-8987