((2R,3R,4S,5R,6S)-5-Allyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol

Base Information

• Chemical Name: ((2R,3R,4S,5R,6S)-5-Allyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol
• CAS No.: 304672-07-9
• Molecular Formula: C₃₁H₃₆O₆
• Molecular Weight: 504.623

Synonyms:((2R,3R,4S,5R,6S)-5-Allyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol

Chemical Property of ((2R,3R,4S,5R,6S)-5-Allyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol

Chemical Property:

Purity/Quality:

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Technology Process of ((2R,3R,4S,5R,6S)-5-Allyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol

There total 3 articles about ((2R,3R,4S,5R,6S)-5-Allyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol 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: 95.0%

(2R,4aR,6S,7R,8S,8aR)-7-Allyl-7,8-bis-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine → ((2R,3R,4S,5R,6S)-5-Allyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol (304672-07-9)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In diethyl ether; dichloromethane; for 0.25h;

DOI:10.3987/com-00-8987

Reference yield:

benzyl bromide (100-39-0) → ((2R,3R,4S,5R,6S)-5-Allyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol (304672-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaH / dimethylformamide / 20 °C

2: 95 percent / LiAlH₄; AlCl₃ / diethyl ether; CH₂Cl₂ / 0.25 h

With lithium aluminium tetrahydride; aluminium trichloride; sodium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3987/com-00-8987

Reference yield:

(2R,4aR,6S,7R,8S,8aR)-7-Allyl-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (304671-79-2) → ((2R,3R,4S,5R,6S)-5-Allyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol (304672-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaH / dimethylformamide / 20 °C

2: 95 percent / LiAlH₄; AlCl₃ / diethyl ether; CH₂Cl₂ / 0.25 h

With lithium aluminium tetrahydride; aluminium trichloride; sodium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3987/com-00-8987

upstream raw materials:

benzyl bromide

(2R,4aR,6S,7R,8S,8aR)-7-Allyl-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Downstream raw materials:

(2S,3S,4S,5R,6S)-5-Allyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde

(2S,3R,4S,5R,6R)-3-Allyl-3,4,5-tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran

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