benzyl (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside

Base Information

• Chemical Name: benzyl (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside
• CAS No.: 105592-35-6
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359
• Mol file: 105592-35-6.mol

Synonyms:benzyl (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside

Chemical Property of benzyl (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of benzyl (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside

There total 3 articles about benzyl (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside 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: 77.0%

methyl uronate (108182-77-0) → benzyl (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside (105592-35-6)

Guidance literature:

With diisobutylaluminum hydride; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1016/0008-6215(86)80004-0

Reference yield:

1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose (74912-02-0,79940-48-0,94118-99-7,20689-03-6) → benzyl (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside (105592-35-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 96.5 percent / sodium periodate / dioxane; H₂O / 1 h / Ambient temperature

2: 98 percent / methanol / 2 h / 0 °C

3: 77 percent / di-isobutylaluminium hydride / CH₂Cl₂ / 3 h / 0 °C

With sodium periodate; diisobutylaluminum hydride; In 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1016/0008-6215(86)80004-0

Reference yield:

benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside (102919-04-0,102854-75-1) → benzyl (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside (105592-35-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / methanol / 2 h / 0 °C

2: 77 percent / di-isobutylaluminium hydride / CH₂Cl₂ / 3 h / 0 °C

With diisobutylaluminum hydride; In methanol; dichloromethane;

DOI:10.1016/0008-6215(86)80004-0

upstream raw materials:

methyl uronate

1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose

benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside

Downstream raw materials:

volemitol

benzyl 7-O-[bis(benzyloxy)phosphoryl]-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside

benzyl 7-O-[bis(benzyloxy)phosphoryl]-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-(Z)-hept-5-enofuranoside

(1S,2S)-1-((3aR,4S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propane-1,2,3-triol