methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside
• CAS No.: 138875-24-8
• Molecular Formula: C₂₈H₃₀O₆
• Molecular Weight: 462.543
• Mol file: 138875-24-8.mol

Synonyms:methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside

Chemical Property of methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside

There total 3 articles about methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside 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:

(2R,3S,4R,5R)-3,4,5-Tris-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran (128184-62-3) → methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside (138875-24-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) dicyclohexylborane, 2) 3M aq. NaOH, 30percent H₂O₂ / 1) THF, 25 deg C, 1.5h, 2) H₂O, 50 deg C, 20 min

2: 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

With sodium hydroxide; oxalyl dichloride; bis(cyclohexanyl)borane; dihydrogen peroxide; dimethyl sulfoxide; triethylamine;

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

Reference yield:

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-idopyranoside (1385089-78-0) → methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside (138875-24-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / toluene / 2.17 h / -30 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.42 h / -78 °C

2.2: -78 °C / Molecular sieve

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; In dichloromethane; toluene; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;

DOI:10.1016/j.carres.2017.04.007

Reference yield:

methyl 2,3-di-O-benzyl-β-D-idopyranoside (1385089-80-4) → methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside (138875-24-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 12 h / 25 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 14 h / 25 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.42 h / -78 °C

4.2: -78 °C / Molecular sieve

With pyridine; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; mineral oil; 4.1: |Swern Oxidation / 4.2: |Swern Oxidation;

DOI:10.1016/j.carres.2017.04.007

upstream raw materials:

(2R,3S,4R,5R)-3,4,5-Tris-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran

methyl 2,3-di-O-benzyl-β-D-idopyranoside

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-idopyranoside

Downstream raw materials:

cyclophellitol

Methanesulfonic acid (1S,2R,3R,4R,5R,6S)-3-(diethyl-isopropyl-silanyloxy)-2-(diethyl-isopropyl-silanyloxymethyl)-4,5,6-trihydroxy-cyclohexyl ester

(2S,3R,4S,5R,6R)-2,3,4-tribenzyloxy-5-hydroxy-6-hydroxymethylcyclohexanone

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