169895-48-1

Basic information

• Product Name: (E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol
• Synonyms: (E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol
• CAS NO: 169895-48-1
• Molecular Weight: 554.842
• Mol File: 169895-48-1.mol

Chemical Properties

• CAS DataBase Reference: (E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol(169895-48-1)
• EPA Substance Registry System: (E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-en-1-ol(169895-48-1)

Safety Data

• Hazardous Substances Data: 169895-48-1(Hazardous Substances Data)

Upstream product

• 169895-46-9 [(2R,3S,4S,6R)-2-Allyl-4-benzyloxy-6-(3-benzyloxy-propyl)-tetrahydro-pyran-3-yloxy]-triethyl-silane 
• 169895-44-7 (2R,3S,4S,6R)-2-Allyl-6-(3-benzyloxy-propyl)-tetrahydro-pyran-3,4-diol 
• 169895-45-8 (2R,3S,4S,6R)-2-Allyl-4-benzyloxy-6-(3-benzyloxy-propyl)-tetrahydro-pyran-3-ol 
• 169895-74-3 (3aR,4R,6R,7aS)-4-Allyl-6-(3-benzyloxy-propyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 132375-60-1 3-((3aR,4R,6R,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-propan-1-ol 
• 100-39-0 benzyl bromide 
• 169895-47-0 (E)-4-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-methyl-but-2-enoic acid ethyl ester 

Downstream Products

• 169895-50-5 (E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester 
• 169895-51-6 (E)-3-{(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester 
• 169895-53-8 (E)-3-[(2R,3S,4aR,6R,8S,8aS)-3-Acetoxy-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acrylic acid methyl ester 
• 169895-52-7 (E)-3-[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-2-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acrylic acid methyl ester 
• 169895-49-2 {(2S,3S)-3-[(2R,3S,4S,6R)-4-Benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-2-methyl-oxiranyl}-methanol 

Relevant articles and documents

Stereocontrolled Total Synthesis of Hemibrevetoxin B

The stereocontrolled total synthesis of hemibrevetoxin B (1) has been achieved in 56 steps and 0.75% overall yield from D-mannose. The intramolecular reaction of γ-alkoxyallylstannane with aldehyde is a key step for the present total synthesis. Thus, the BF3·OEt2-mediated reaction of 24 gave 6 as a sole product. We encountered difficulty in the synthesis of γ-alkoxyallylstannane 30 from the corresponding allyl ether 29 in which the γ-alkoxy substituent became sterically quite bulky. This problem was solved by developing the acetal cleavage method for the synthesis of γ-alkoxyallylstannanes. The cyclization of 38 proceeded smoothly to give the key intermediate 5 in a highly stereoselective manner. Construction of the α-vinyl aldehyde and (Z)-diene moieties were performed using Nicolaou's protocol.