(2R,3S,4S)-3-O-Benzyl-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetrol

Base Information

• Chemical Name: (2R,3S,4S)-3-O-Benzyl-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetrol
• CAS No.: 121964-06-5
• Molecular Formula: C₁₆H₂₄O₄
• Molecular Weight: 280.364

Synonyms:(2R,3S,4S)-3-O-Benzyl-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetrol

Chemical Property of (2R,3S,4S)-3-O-Benzyl-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetrol

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Technology Process of (2R,3S,4S)-3-O-Benzyl-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetrol

There total 2 articles about (2R,3S,4S)-3-O-Benzyl-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-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: 73.0%

C18H27NO4 (1078118-69-0) → (2R,3S,4S)-3-O-Benzyl-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetrol (121964-06-5)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1021/jo801728s

Reference yield:

(2R,3S,4S)-3-Bnzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol (100572-69-8) → (2R,3S,4S)-3-O-Benzyl-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetrol (121964-06-5)

Guidance literature:

With sodium tetrahydroborate; ozone; Yield given. Multistep reaction; 1.) MeOH, -78 degC, 2.) 20 degC;

DOI:10.1021/ja00201a033

Reference yield: 92.0%

(2R,3S,4S)-3-O-Benzyl-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetrol (121964-06-5) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (2S,3S)-3-benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propyl ester (121964-11-2)

Guidance literature:

With pyridine; dmap; In tetrahydrofuran; 1.) 14 h, 20 degC, 2.) 2 h, 45 degC;

DOI:10.1021/ja00201a033

upstream raw materials:

(2R,3S,4S)-3-Bnzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol

C₁₈H₂₇NO₄

Downstream raw materials:

Methanesulfonic acid (2S,3S)-3-benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propyl ester

(2R,3S,4S)-5-Azido-3-O-benzyl-4-methylpentane-1,2,3-triol

Benzoic acid (2R,3S,4S)-5-azido-3-benzyloxy-2-hydroxy-4-methyl-pentyl ester

Toluene-4-sulfonic acid (2R,3S,4S)-5-azido-3-benzyloxy-2-hydroxy-4-methyl-pentyl ester

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