(2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal oxime

Base Information

• Chemical Name: (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal oxime
• CAS No.: 86496-30-2
• Molecular Formula: C₃₄H₃₇NO₆
• Molecular Weight: 555.671
• Mol file: 86496-30-2.mol

Synonyms:(2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal oxime

Chemical Property of (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal oxime

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal oxime

There total 5 articles about (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal 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: 99.0%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal oxime (86496-30-2)

Guidance literature:

With hydroxylamine hydrochloride; sodium ethanolate; In ethanol; at 55 - 60 ℃; for 7h;

DOI:10.1002/hlca.19910740839

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal oxime (86496-30-2) + (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal oxime

Guidance literature:

With hydroxylamine hydrochloride; sodium; In ethanol; at 60 ℃; for 6h; Title compound not separated from byproducts;

Reference yield:

methyl D-glucopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6,3149-68-6) → (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal oxime (86496-30-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / 120 °C

2: sulfuric acid; acetic acid / 90 °C

3: ethanol; hydroxylamine hydrochloride; sodium / 74 °C

With ethanol; sulfuric acid; hydroxylamine hydrochloride; sodium; sodium hydride; acetic acid;

DOI:10.3390/molecules16119495

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

methyl D-glucopyranoside

methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside

benzyl chloride

Downstream raw materials:

C₃₅H₃₇NO₈S

1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-hydrazi-D-glucitol

1-Azi-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose

(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-one oxime