(2R,3S,4R)-3-benzyloxy-2-benzyloxymethyl-4-(phenylselenyl)tetrahydrofuran

Base Information

• Chemical Name: (2R,3S,4R)-3-benzyloxy-2-benzyloxymethyl-4-(phenylselenyl)tetrahydrofuran
• CAS No.: 334784-85-9
• Molecular Formula: C₂₅H₂₆O₃Se
• Molecular Weight: 453.44
• Mol file: 334784-85-9.mol

Synonyms:(2R,3S,4R)-3-benzyloxy-2-benzyloxymethyl-4-(phenylselenyl)tetrahydrofuran

Chemical Property of (2R,3S,4R)-3-benzyloxy-2-benzyloxymethyl-4-(phenylselenyl)tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-3-benzyloxy-2-benzyloxymethyl-4-(phenylselenyl)tetrahydrofuran

There total 6 articles about (2R,3S,4R)-3-benzyloxy-2-benzyloxymethyl-4-(phenylselenyl)tetrahydrofuran 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: 37.0%

N-phenylselanylphthalimide (71098-88-9) + (2R,3R)-1,3-di-O-benzyl-4-pentene-1,2,3-triol (220788-30-7) → (2R,3S,4R)-3-benzyloxy-2-benzyloxymethyl-4-(phenylselenyl)tetrahydrofuran (334784-85-9) + (2R,3S,4S)-3-benzyloxy-2-benzyloxymethyl-4-(phenylselenyl)tetrahydrofuran (334784-86-0)

Guidance literature:

With camphor-10-sulfonic acid; In 1,2-dichloro-ethane; for 0.333333h; Heating;

DOI:10.1002/1099-0690(200102)2001:3<507::AID-EJOC507>3.0.CO;2-R

Reference yield:

(4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol (212579-64-1) → (2R,3S,4R)-3-benzyloxy-2-benzyloxymethyl-4-(phenylselenyl)tetrahydrofuran (334784-85-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran

2.1: 100 percent / Dowex 50 W/H⁺ acid resin / methanol / 2 h / 20 °C

3.1: 4-Angstroem molecular sieves; Bu₂SnO / toluene / 48 h / 110 °C

3.2: 67 percent / Bu₄NBr / toluene / 48 h / 70 °C

4.1: 37 percent / camphorsulfonic acid / 1,2-dichloro-ethane / 0.33 h / Heating

With 4 A molecular sieve; Dowex 50 W; H⁺ acid resin; camphor-10-sulfonic acid; sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; toluene;

DOI:10.1002/1099-0690(200102)2001:3<507::AID-EJOC507>3.0.CO;2-R

Reference yield:

(2R,3R)-3-O-benzyl-1,2-O-isopropylidene-4-pentene-1,2,3-triol (108341-87-3) → (2R,3S,4R)-3-benzyloxy-2-benzyloxymethyl-4-(phenylselenyl)tetrahydrofuran (334784-85-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 100 percent / Dowex 50 W/H⁺ acid resin / methanol / 2 h / 20 °C

2.1: 4-Angstroem molecular sieves; Bu₂SnO / toluene / 48 h / 110 °C

2.2: 67 percent / Bu₄NBr / toluene / 48 h / 70 °C

3.1: 37 percent / camphorsulfonic acid / 1,2-dichloro-ethane / 0.33 h / Heating

With 4 A molecular sieve; Dowex 50 W; H⁺ acid resin; camphor-10-sulfonic acid; di(n-butyl)tin oxide; In methanol; 1,2-dichloro-ethane; toluene;

DOI:10.1002/1099-0690(200102)2001:3<507::AID-EJOC507>3.0.CO;2-R

upstream raw materials:

N-phenylselanylphthalimide

(2R,3R)-1,3-di-O-benzyl-4-pentene-1,2,3-triol

benzyl bromide

(4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol

Downstream raw materials:

1,4-anhydro-3,5-di-O-benzyl-2-deoxy-D-threo-pent-1-enitol