1,2-Dideoxy-2-ethenyl-4,5-O-(1-methylethylidene)-D-erythro-pentitol

Base Information

• Chemical Name: 1,2-Dideoxy-2-ethenyl-4,5-O-(1-methylethylidene)-D-erythro-pentitol
• CAS No.: 88406-01-3
• Molecular Formula: C₁₀H₁₈O₃
• Molecular Weight: 186.251
• DSSTox Substance ID: DTXSID401162479
• Nikkaji Number: J1.914.491G
• Mol file: 88406-01-3.mol

Synonyms:DTXSID401162479;1,2-Dideoxy-2-ethenyl-4,5-O-(1-methylethylidene)-D-erythro-pentitol;(4R)-2,2-Dimethyl-4beta-[(1S,2R)-1-hydroxy-2-methyl-3-butenyl]-1,3-dioxolane;88406-01-3

Chemical Property of 1,2-Dideoxy-2-ethenyl-4,5-O-(1-methylethylidene)-D-erythro-pentitol

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 186.125594432
• Heavy Atom Count: 13
• Complexity: 189

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C=C)C(C1COC(O1)(C)C)O
• Isomeric SMILES: C[C@H](C=C)[C@@H]([C@H]1COC(O1)(C)C)O

Technology Process of 1,2-Dideoxy-2-ethenyl-4,5-O-(1-methylethylidene)-D-erythro-pentitol

There total 1 articles about 1,2-Dideoxy-2-ethenyl-4,5-O-(1-methylethylidene)-D-erythro-pentitol 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:

(Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (69611-01-4) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → (Z)-2-Butene (590-18-1) + (1R,2R)-2-methyl-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol (88424-94-6) + 2,3-O-isopropylidene-1-C-<(1R)-1-methylprop-2-enyl>-D-erythro-glycerol (88406-01-3) + 2,3-O-isopropylidene-1-C-<(1S)-1-methylprop-2-enyl>-D-erythro-glycerol (88424-95-7)

Guidance literature:

In dichloromethane; -78 deg C to r. t.;

DOI:10.1021/ja00272a043

Reference yield: 98.0%

2,3-O-isopropylidene-1-C-<(1R)-1-methylprop-2-enyl>-D-erythro-glycerol (88406-01-3) + benzyl bromide (100-39-0) → (R)-4-((1S,2R)-1-benzyloxy-2-methylbut-3-enyl)-2,2-dimethyl-[1,3]dioxolane (109121-41-7)

Guidance literature:

2,3-O-isopropylidene-1-C-<(1R)-1-methylprop-2-enyl>-D-erythro-glycerol; With sodium iodide; In N,N-dimethyl-formamide; at 0 ℃; for 0.0833333h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

DOI:10.1039/d1ob00661d

Reference yield: 93.0%

2,3-O-isopropylidene-1-C-<(1R)-1-methylprop-2-enyl>-D-erythro-glycerol (88406-01-3) + p-methoxybenzyl chloride (824-94-2) → (3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexene (377750-95-3)

Guidance literature:

2,3-O-isopropylidene-1-C-<(1R)-1-methylprop-2-enyl>-D-erythro-glycerol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

p-methoxybenzyl chloride; In N,N-dimethyl-formamide; at 0 ℃; for 2h; Further stages.;

DOI:10.1021/ol016449u

upstream raw materials:

(Z)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

(R)-4-((1S,2R)-1-benzyloxy-2-methylbut-3-enyl)-2,2-dimethyl-[1,3]dioxolane

(3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexene

(S)-((1S,2R)-1-benzyloxy-2-methyl-but-3-enyl)-oxirane

(2S,3S,4R)-3-benzyloxy-1-methoxy-4-methyl-hex-5-en-2-ol