(3R,4S,5R)-3-(cyclohexyloxydimethyl)silyl-5,6-O-isopropylidene-hex-1-ene-4-ol

Base Information

• Chemical Name: (3R,4S,5R)-3-(cyclohexyloxydimethyl)silyl-5,6-O-isopropylidene-hex-1-ene-4-ol
• CAS No.: 133285-36-6
• Molecular Formula: C₁₇H₃₂O₄Si
• Molecular Weight: 328.524

Synonyms:(3R,4S,5R)-3-(cyclohexyloxydimethyl)silyl-5,6-O-isopropylidene-hex-1-ene-4-ol

Chemical Property of (3R,4S,5R)-3-(cyclohexyloxydimethyl)silyl-5,6-O-isopropylidene-hex-1-ene-4-ol

Chemical Property:

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Technology Process of (3R,4S,5R)-3-(cyclohexyloxydimethyl)silyl-5,6-O-isopropylidene-hex-1-ene-4-ol

There total 3 articles about (3R,4S,5R)-3-(cyclohexyloxydimethyl)silyl-5,6-O-isopropylidene-hex-1-ene-4-ol 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: 67.0%

(4R,5R)-2-[(E)-3-(Cyclohexyloxy-dimethyl-silanyl)-allyl]-[1,3,2]dioxaborolane-4,5-dicarboxylic acid diisopropyl ester (133321-84-3) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → (3R,4S,5R)-3-(cyclohexyloxydimethyl)silyl-5,6-O-isopropylidene-hex-1-ene-4-ol (133285-36-6) + (3S,4R,5R)-3-(cyclohexyloxydimethyl)silyl-5,6-O-isopropylidene-hex-1-ene-4-ol (133321-85-4)

Guidance literature:

With 4 A molecular sieve; In toluene; at -78 ℃; for 24h;

DOI:10.1016/S0040-4020(01)88869-4

Reference yield: 2.0%

(4S,5S)-2-[(E)-3-(Cyclohexyloxy-dimethyl-silanyl)-allyl]-[1,3,2]dioxaborolane-4,5-dicarboxylic acid diisopropyl ester (133285-35-5) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → (3R,4S,5R)-3-(cyclohexyloxydimethyl)silyl-5,6-O-isopropylidene-hex-1-ene-4-ol (133285-36-6) + (3S,4R,5R)-3-(cyclohexyloxydimethyl)silyl-5,6-O-isopropylidene-hex-1-ene-4-ol (133321-85-4)

Guidance literature:

With 4 A molecular sieve; In toluene; at -78 ℃; for 24h;

DOI:10.1016/S0040-4020(01)88869-4

Reference yield:

allyldimethylsilyl cyclohexyl ether (81194-47-0) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → (3R,4S,5R)-3-(cyclohexyloxydimethyl)silyl-5,6-O-isopropylidene-hex-1-ene-4-ol (133285-36-6)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(00)97299-X

upstream raw materials:

allyldimethylsilyl cyclohexyl ether

2,3-isopropylidene-glyceraldehyde

(4S,5S)-2-[(E)-3-(Cyclohexyloxy-dimethyl-silanyl)-allyl]-[1,3,2]dioxaborolane-4,5-dicarboxylic acid diisopropyl ester

(4R,5R)-2-[(E)-3-(Cyclohexyloxy-dimethyl-silanyl)-allyl]-[1,3,2]dioxaborolane-4,5-dicarboxylic acid diisopropyl ester

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