(2S,3S,4R,5R)-2,4-Bis-benzyloxy-5-benzyloxymethyl-3-bromo-tetrahydro-furan

Base Information

Chemical Name:(2S,3S,4R,5R)-2,4-Bis-benzyloxy-5-benzyloxymethyl-3-bromo-tetrahydro-furan
CAS No.:80765-82-8
Molecular Formula:C₂₆H₂₇BrO₄
Molecular Weight:483.402
Hs Code.:

Synonyms:(2S,3S,4R,5R)-2,4-Bis-benzyloxy-5-benzyloxymethyl-3-bromo-tetrahydro-furan

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Chemical Property of (2S,3S,4R,5R)-2,4-Bis-benzyloxy-5-benzyloxymethyl-3-bromo-tetrahydro-furan

Chemical Property:

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Technology Process of (2S,3S,4R,5R)-2,4-Bis-benzyloxy-5-benzyloxymethyl-3-bromo-tetrahydro-furan

There total 5 articles about (2S,3S,4R,5R)-2,4-Bis-benzyloxy-5-benzyloxymethyl-3-bromo-tetrahydro-furan 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: 72.0%

: 80765-79-3
1,3,5-tri-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranose

: 80765-82-8
(2S,3S,4R,5R)-2,4-Bis-benzyloxy-5-benzyloxymethyl-3-bromo-tetrahydro-furan

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium bromide; In dimethyl sulfoxide; for 5h; Ambient temperature;
DOI:10.1021/jo00347a027

Reference yield:

: 16054-77-6
(3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2,3-diol

: 80765-82-8
(2S,3S,4R,5R)-2,4-Bis-benzyloxy-5-benzyloxymethyl-3-bromo-tetrahydro-furan

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) dibutyltin oxide, 2.) potassium carbonate / 1.) methanol, reflux, 1.5 h, 2.) DMF, RT, 12 h

2: 89.7 percent / pyridine / CH₂Cl₂ / 1.5 h / -20 °C

3: 72 percent / HMPA, LiBr / dimethylsulfoxide / 5 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; di(n-butyl)tin oxide; potassium carbonate; lithium bromide; In dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo00347a027

Reference yield:

: 100-39-0
benzyl bromide

: 80765-82-8
(2S,3S,4R,5R)-2,4-Bis-benzyloxy-5-benzyloxymethyl-3-bromo-tetrahydro-furan

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) dibutyltin oxide, 2.) potassium carbonate / 1.) methanol, reflux, 1.5 h, 2.) DMF, RT, 12 h

2: 89.7 percent / pyridine / CH₂Cl₂ / 1.5 h / -20 °C

3: 72 percent / HMPA, LiBr / dimethylsulfoxide / 5 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; di(n-butyl)tin oxide; potassium carbonate; lithium bromide; In dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo00347a027