N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-1,5,7-trideoxy-1,5-imino-2,3-O-isopropylidene-L-glycero-L-manno-octitol

Base Information

• Chemical Name: N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-1,5,7-trideoxy-1,5-imino-2,3-O-isopropylidene-L-glycero-L-manno-octitol
• CAS No.: 121251-77-2
• Molecular Formula: C₃₁H₄₇NO₅Si
• Molecular Weight: 541.803
• Mol file: 121251-77-2.mol

Synonyms:

Chemical Property of N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-1,5,7-trideoxy-1,5-imino-2,3-O-isopropylidene-L-glycero-L-manno-octitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-1,5,7-trideoxy-1,5-imino-2,3-O-isopropylidene-L-glycero-L-manno-octitol

There total 8 articles about N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-1,5,7-trideoxy-1,5-imino-2,3-O-isopropylidene-L-glycero-L-manno-octitol 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:

benzyl bromide (100-39-0) → N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-1,5,7-trideoxy-1,5-imino-2,3-O-isopropylidene-L-glycero-L-manno-octitol (121251-77-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / NaH, Bu₄NI / tetrahydrofuran

2: 76 percent / LiAlH₄, AlCl₃

3: oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / -40 °C

4: 80 percent / tetrahydrofuran / Ambient temperature

With lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(88)85305-X

Reference yield:

N-benzyl-4-O-benzyl-1,5-dideoxy-1,5-imino-2,3-O-isopropylidene-L-mannitol (121251-74-9) → N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-1,5,7-trideoxy-1,5-imino-2,3-O-isopropylidene-L-glycero-L-manno-octitol (121251-77-2)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / -40 °C

2: 80 percent / tetrahydrofuran / Ambient temperature

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(88)85305-X

Reference yield:

(3aS,6R,7S,7aS)-5-Benzyl-7-benzyloxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carbaldehyde (121194-99-8) → N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-1,5,7-trideoxy-1,5-imino-2,3-O-isopropylidene-L-glycero-L-manno-octitol (121251-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / tetrahydrofuran / Ambient temperature

In tetrahydrofuran;

DOI:10.1016/0040-4039(88)85305-X

upstream raw materials:

N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-1,5,7,8-tetradeoxy-1,5-imino-2,3-O-isopropylidene-DL-glycero-L-manno-oct-7-enitol

N-benzyl-4-O-benzyl-1,5,7,8-tetradeoxy-1,5-imino-2,3-O-isopropylidene-DL-glycero-L-manno-oct-7-enitol

tert-butyldimethylsilyl chloride

benzyl bromide

Downstream raw materials:

L-6-epicastanospermine

(3aS,8R,8aR,9S,9aS)-5-Benzyl-9-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-f]indolizin-5-ium

(3aS,8R,8aR,9S,9aS)-9-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-f]indolizine

N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-(1S,6S,7S,8S,8aS)-1,6,7,8-tetrahydroxyoctahydroindolizinium methanesulphonate