(2R,3S)-3-O-benzyl-4-iodo-1,2-O-isopropylidenebutane-1,2,3-triol

Base Information

• Chemical Name: (2R,3S)-3-O-benzyl-4-iodo-1,2-O-isopropylidenebutane-1,2,3-triol
• CAS No.: 115689-96-8
• Molecular Formula: C₁₄H₁₉IO₃
• Molecular Weight: 362.208
• Mol file: 115689-96-8.mol

Synonyms:(2R,3S)-3-O-benzyl-4-iodo-1,2-O-isopropylidenebutane-1,2,3-triol

Chemical Property of (2R,3S)-3-O-benzyl-4-iodo-1,2-O-isopropylidenebutane-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-O-benzyl-4-iodo-1,2-O-isopropylidenebutane-1,2,3-triol

There total 11 articles about (2R,3S)-3-O-benzyl-4-iodo-1,2-O-isopropylidenebutane-1,2,3-triol 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: 95.0%

Methanesulfonic acid (R)-2-benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester (115689-97-9,115689-99-1,116405-03-9,116499-63-9) → dl-erythro-3-O-benzyl-4-iodo-1,2-O-isopropylidenebutane-1,2,3-triol (115689-96-8,115689-98-0,127000-45-7,127000-46-8)

Guidance literature:

With sodium hydrogencarbonate; sodium iodide; In acetone; for 14h; Heating;

DOI:10.1248/cpb.37.2379

Reference yield: 89.0%

1-methanesulfonyloxy-2-O-benzyl-3,4-O-isopropylidene-D-threitol (115689-97-9) → (2R,3S)-3-O-benzyl-4-iodo-1,2-O-isopropylidenebutane-1,2,3-triol (115689-96-8)

Guidance literature:

With sodium hydrogencarbonate; sodium iodide; In acetone; for 7h; Reflux;

Reference yield:

benzaldehyde (100-52-7) → dl-erythro-3-O-benzyl-4-iodo-1,2-O-isopropylidenebutane-1,2,3-triol (115689-96-8,115689-98-0,127000-45-7,127000-46-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 58 percent / p-TsOH (H₂O) / toluene / 8 h / Heating

2: 65 percent / LiAlH₄-AlCl₃ / diethyl ether; CH₂Cl₂ / 3 h / Ambient temperature

3: 80 percent / p-TsOH (H₂O) / benzene / 3 h / Heating

4: 13.11 g / Et₃N / benzene / 1 h / Ambient temperature

5: 95 percent / NaI, NaHCO₃ / acetone / 14 h / Heating

With lithium aluminium tetrahydride; aluminium trichloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; sodium iodide; toluene-4-sulfonic acid; In diethyl ether; dichloromethane; acetone; toluene; benzene;

DOI:10.1248/cpb.37.2379

upstream raw materials:

1-methanesulfonyloxy-2-O-benzyl-3,4-O-isopropylidene-D-threitol

(R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

2-O-benzyl-L-threitol

(4S,5S)-dimethyl 2-phenyl-1,3-dioxolane-4,5-dicarboxylate

Downstream raw materials:

ethyl (4R,5R)-4-benzyloxy-2-ethoxycarbonyl-5,6-isopropylidenedioxyhexanoate

(2R,3R)-3-benzyloxy-6-(tert-butyldiphenylsiloxy)-1-triphenylmethoxyhexan-2-ol

Methanesulfonic acid (1R,2R)-2-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-1-trityloxymethyl-pentyl ester

<(2S,3R)-3-benzyloxytetrahydropyran-2-yl>methanol