benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside

Base Information

• Chemical Name: benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside
• CAS No.: 106445-48-1
• Molecular Formula: C₃₅H₃₈O₇
• Molecular Weight: 570.683
• Mol file: 106445-48-1.mol

Synonyms:benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside

Chemical Property of benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside

There total 14 articles about benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside 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: 63.0%

benzyl 2,3,4-O-tribenzyl-6,7-dideoxy-α-D-hept-6-enopyranoside (1554004-68-0) → benzyl 2,3,4-tri-O-benzyl-α-D-glycero-D-manno-heptopyranoside (106445-56-1) + benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside (106445-48-1)

Guidance literature:

With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In acetone; at 20 ℃; for 4h;

DOI:10.1016/j.bmc.2013.12.019

Reference yield: 18.3%

(S)-2-Amino-1-((2R,3S,4S,5S,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanol (106445-46-9) → 1-((2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanone (106445-50-5) + benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside (106445-48-1)

Guidance literature:

With acetic acid; sodium nitrite; In 1,4-dioxane; water; 0 deg C, RT, 5 h;

DOI:10.1016/0008-6215(86)80013-1

Reference yield:

(2S,3S,4S,5S,6S)-3,4,5,6-tetrabenzyloxytetrahydropyran-2-carbaldehyde (102046-36-6) → benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside (106445-48-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,2-dibromoethane / tetrahydrofuran / 2 h / 0 °C

2: 1.) NH₄Cl; 2.) H₂O₂ (30percent) / 1.) hydrolysis, 0 deg C; 2.) MeOH/THF, reflux, 15 h

With dihydrogen peroxide; ammonium chloride; ethylene dibromide; In tetrahydrofuran;

DOI:10.1002/recl.19881070706

upstream raw materials:

benzyl 7-O-allyl-2,3,4-tri-O-benzyl-β-L-glycero-D-mannoheptopyranoside

(S)-2-Amino-1-((2R,3S,4S,5S,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanol

(2S,3S,4S,5S,6S)-3,4,5,6-tetrabenzyloxytetrahydropyran-2-carbaldehyde

benzyl 6-O-triphenylmethyl-α-D-mannopyranoside

Downstream raw materials:

L-glycero-D-manno-heptose