(2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal oxime

Base Information

• Chemical Name: (2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal oxime
• CAS No.: 128184-65-6
• Molecular Formula: C₂₈H₃₁NO₅
• Molecular Weight: 461.558
• Mol file: 128184-65-6.mol

Synonyms:(2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal oxime

Chemical Property of (2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal oxime

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal oxime

There total 9 articles about (2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal oxime 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: 100.0%

(2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal (139285-93-1) → 2,3,4-tri-O-benzyl-6,7-dideoxy-D-galacto-hept-6-enose-oxime (128184-65-6,134680-70-9,134731-71-8,139402-97-4,139402-98-5)

Guidance literature:

With pyridine; hydrazine hydrochloride; at 25 ℃; for 3h;

DOI:10.1016/0008-6215(91)89017-A

Reference yield:

(2S,3R,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal (138794-96-4) → (2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal oxime (128184-65-6)

Guidance literature:

With pyridine; hydroxylamine hydrochloride; at 25 ℃; for 1h; Yield given;

DOI:10.1016/S0040-4039(00)88756-0

Reference yield:

methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside (4356-80-3,34212-64-1,40653-32-5,53008-65-4,68027-27-0,73111-53-2,128184-63-4,138794-99-7,55094-38-7,641635-63-4) → 2,3,4-tri-O-benzyl-6,7-dideoxy-D-galacto-hept-6-enose-oxime (128184-65-6,134680-70-9,134731-71-8,139402-97-4,139402-98-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) oxalyl chloride, DMSO, 2) NET₃ / 1) CH₂Cl₂, -78 deg C, 15 min, 2a) -78 deg C, 15 min, 2b) -78 to -40 deg C

2: 91 percent / benzene / 0.17 h / 25 °C

3: 1) Ac₂O, conc. H₂SO₄, 2) NaOMe / 1) 0 deg C, 10 min, 2a) MeOH, 0 deg c, 10 min, 2b) 25 deg C, 0.5h

4: 100 percent / H₂NNH₂*HCl, pyridine / 3 h / 25 °C

With pyridine; oxalyl dichloride; hydrazine hydrochloride; sulfuric acid; sodium methylate; acetic anhydride; dimethyl sulfoxide; triethylamine; In benzene;

DOI:10.1016/0008-6215(91)89017-A

upstream raw materials:

(2S,3R,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal

(2R,3S,4S,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-hept-6-enal

methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside

methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-α-D-galacto-hept-6-enopyranoside

Downstream raw materials:

(1R,2R,3S,4S,5R)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene

(3aR,4R,5S,6R,7S)-5,6,7-Tris-benzyloxy-3,3a,4,5,6,7-hexahydro-benzo[c]isoxazol-4-ol

(1S,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-8-oxa-7-azabicyclo<4.3.0>non-6-ene

1D-4,5,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-chiro-inositol