methyl 4,6-O-benzylidene-2-deoxy-3-C-methyl-α-D-arabino-hexopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-deoxy-3-C-methyl-α-D-arabino-hexopyranoside
• CAS No.: 100100-70-7
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321
• Mol file: 100100-70-7.mol

Synonyms:methyl 4,6-O-benzylidene-2-deoxy-3-C-methyl-α-D-arabino-hexopyranoside

Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-3-C-methyl-α-D-arabino-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-2-deoxy-3-C-methyl-α-D-arabino-hexopyranoside

There total 14 articles about methyl 4,6-O-benzylidene-2-deoxy-3-C-methyl-α-D-arabino-hexopyranoside 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: 94.0%

methylmagnesium bromide (75-16-1) + (2R,6S)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one (6752-49-4,10578-82-2,18424-63-0,63598-31-2,66101-30-2,77481-65-3,77481-68-6,126254-99-7,131615-77-5) → (2R,6S,8S)-6-Methoxy-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (6752-52-9,13264-07-8,18424-64-1,19231-32-4,77481-74-4,77481-75-5,77481-76-6,77481-77-7,78086-67-6,100100-70-7)

Guidance literature:

DOI:10.1080/00397919108016788

Reference yield: 63.0%

Methyl-4,6-O-benzyliden-2-desoxy-3-C-tosyloxymethyl-α-D-arabino-hexopyranosid (99967-12-1) → methyl 4,6-O-benzylidene-2-deoxy-3-C-methyl-α-D-arabino-hexopyranoside (100100-70-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 2h;

DOI:10.1002/jlac.198619860403

Reference yield:

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose (63598-31-2) → methyl 4,6-O-benzylidene-2-deoxy-3-C-methyl-α-D-arabino-hexopyranoside (100100-70-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-C₄H₉Li / 1.) THF, 30 min, RT 2.) THF, -25 deg C, 3 h; 18 h, RT

2: 90 percent / OsO₄, N-methylmorpholine-N-oxide dihydrate / acetone; H₂O / 20 h / 40 °C

3: 81 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

4: 26 percent / pyridine / CH₂Cl₂ / 1.) 0 deg C, 3 h 2.) room temperature, 5 d

5: 63 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

With pyridine; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; 4-methylmorpholine N-oxide; In diethyl ether; dichloromethane; water; acetone;

DOI:10.1002/jlac.198619860403

upstream raw materials:

methyl magnesium iodide

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose

(4aR,6S,8aR)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

methyl iodide

Downstream raw materials:

Benzoic acid (2S,3R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester

C₂₈H₃₆O₇

C₂₈H₃₆O₇

Benzoic acid (2R,3R,4R,6S)-3-((2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl ester

Refernces

• 1、 Beau, Jean-Marie,Jaurand, Guy,Esnault, Jacques,Sinay, Pierre. "SYNTHESIS OF THE DISACCHARIDE C-D FRAGMENT FOUND IN EVERNINOMICIN-C AND -D, AVALAMYCIN-A AND -C, AND CURAMYCIN-A: STEREOCHEMISTRY AT THE SPIRO-ORTHOLACTONE CENTER". . p. 1105 - 1108. Retrieved 2007/10/02.
• 2、 Dyong, Ingolf,Schulte, Gerhard. "Synthesen biologisch wichtiger Kohlenhydrate, 24. Derivate des Sibirosamins (4,6-Didesoxy-3-C-methyl-4-methylamino-D-altropyranose) durch 4 -> 2-Chiralitaetstransfer und vic. cis-Oxyaminierung eines 3-C-Methyl-hex-3-enopyranosids". . p. 1484 - 1502. Retrieved 2007/10/02.