2,3,4,5-tetra-O-benzyl diethyl dithioacetal D-lyxose

Base Information

• Chemical Name: 2,3,4,5-tetra-O-benzyl diethyl dithioacetal D-lyxose
• CAS No.: 135983-28-7
• Molecular Formula: C₃₇H₄₄O₄S₂
• Molecular Weight: 616.886
• Mol file: 135983-28-7.mol

Synonyms:2,3,4,5-tetra-O-benzyl diethyl dithioacetal D-lyxose

Chemical Property of 2,3,4,5-tetra-O-benzyl diethyl dithioacetal D-lyxose

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,5-tetra-O-benzyl diethyl dithioacetal D-lyxose

There total 1 articles about 2,3,4,5-tetra-O-benzyl diethyl dithioacetal D-lyxose 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: 92.0%

(2R,3S,4S)-5,5-bis(ethylthio)pentane-1,2,3,4-tetraol (6838-08-0) + benzyl bromide (100-39-0) → 2,3,4,5-tetra-O-benzyl diethyl dithioacetal D-lyxose (135983-28-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c8cc05523h

Reference yield: 69.0%

2,3,4,5-tetra-O-benzyl diethyl dithioacetal D-lyxose (135983-28-7) → (2S,3S,4R)-2,3,4,5-tetrakis(benzyloxy)pentanal (135983-29-8)

Guidance literature:

With water; iodine; sodium hydrogencarbonate; In acetone; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b01878

Reference yield:

2,3,4,5-tetra-O-benzyl diethyl dithioacetal D-lyxose (135983-28-7) → ethyl 2,3,4,5-tetra-O-benzyl-1’,1’-difluoro-1-hydroxyheptanoate + ethyl 2,3,4,5-tetra-O-benzyl-1’,1’-difluoro-1-hydroxyheptanoate

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate; iodine; water / acetone / 2.5 h / 20 °C / Inert atmosphere

2: zinc; chloro-trimethyl-silane / tetrahydrofuran / 1.5 h / 60 °C / Inert atmosphere

With chloro-trimethyl-silane; water; iodine; sodium hydrogencarbonate; zinc; In tetrahydrofuran; acetone; 2: |Reformatsky Reaction;

DOI:10.1021/acs.orglett.9b01878

upstream raw materials:

(2R,3S,4S)-5,5-bis(ethylthio)pentane-1,2,3,4-tetraol

benzyl bromide

Downstream raw materials:

(2S,3S,4R)-2,3,4,5-tetrakis(benzyloxy)pentanal

C₄₈H₅₂O₇PN

Trimethyl-((2S,3S,4R)-2,3,4,5-tetrakis-benzyloxy-1-trifluoromethyl-pentyloxy)-silane

(3R,4S,5R)-3,4,5,6-Tetrakis-benzyloxy-1,1,1-trifluoro-hexan-2-ol