(1S,6S,2R)-8,8-dimethyl-4,7,9-trioxa-5-(phenylmethoxy)bicyclo<4.3.0>nonan-2-ol

Base Information

• Chemical Name: (1S,6S,2R)-8,8-dimethyl-4,7,9-trioxa-5-(phenylmethoxy)bicyclo<4.3.0>nonan-2-ol
• CAS No.: 184481-19-4
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321

Synonyms:(1S,6S,2R)-8,8-dimethyl-4,7,9-trioxa-5-(phenylmethoxy)bicyclo<4.3.0>nonan-2-ol

Chemical Property of (1S,6S,2R)-8,8-dimethyl-4,7,9-trioxa-5-(phenylmethoxy)bicyclo<4.3.0>nonan-2-ol

Chemical Property:

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Technology Process of (1S,6S,2R)-8,8-dimethyl-4,7,9-trioxa-5-(phenylmethoxy)bicyclo<4.3.0>nonan-2-ol

There total 5 articles about (1S,6S,2R)-8,8-dimethyl-4,7,9-trioxa-5-(phenylmethoxy)bicyclo<4.3.0>nonan-2-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: 90.0%

(5S,3R,4R)-2-(phenylmethoxy)perhydro-2H-pyran-3,4,5-triol (184481-18-3) + 2,2-dimethoxy-propane (77-76-9) → (1S,6S,2R)-8,8-dimethyl-4,7,9-trioxa-5-(phenylmethoxy)bicyclo<4.3.0>nonan-2-ol (184481-19-4)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 24h; Ambient temperature;

DOI:10.1021/ja9826688

Reference yield: 90.0%

(5S,3R,4R)-2-(phenylmethoxy)perhydro-2H-pyran-3,4,5-triol (184481-18-3) + acetone (67-64-1) → (1S,6S,2R)-8,8-dimethyl-4,7,9-trioxa-5-(phenylmethoxy)bicyclo<4.3.0>nonan-2-ol (184481-19-4)

Guidance literature:

With phthalic acid dimethyl ester; toluene-4-sulfonic acid;

DOI:10.1021/jo961619f

Reference yield:

D-lyxose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → (1S,6S,2R)-8,8-dimethyl-4,7,9-trioxa-5-(phenylmethoxy)bicyclo<4.3.0>nonan-2-ol (184481-19-4)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH*H₂O / 48 h / 60 °C

2: 90 percent / p-TsOH*H₂O / acetone / 24 h / Ambient temperature

With toluene-4-sulfonic acid; In acetone;

DOI:10.1021/ja9826688

upstream raw materials:

(5S,3R,4R)-2-(phenylmethoxy)perhydro-2H-pyran-3,4,5-triol

acetone

2,2-dimethoxy-propane

D-lyxose

Downstream raw materials:

1-<(6S,1R,2R)-8,8-dimethyl-4,7,9-trioxa-5-(phenylmethoxy)bicyclo<4.3.0>non-2-yloxy>-1,1,2,2-tetramethyl-1-silapropane

C₁₈H₂₆O₆

methyl 6-<(4S,7S,7aS,3aR)-7-hydroxy-2,2-dimethyl-4-<(phenylmethoxy)amino>-6-phenylthio-2,3,4,7,3a,7a-hexahydro-1,3-dioxainden-5-yl>-2H-benzo1,3-dioxolane-5-carboxylate

6-((3R)-3-<(4R,5R)-5-<2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>-3-(1,1,2,2-tetramethyl-1-silapropoxy)prop-1-ynyl)-2H-benzo1,3-dioxolene-5-carbaldehyde

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