(2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-3-(S)-oxiranyl-2,3-dihydro-naphtho[1,2-b]furan

Base Information

• Chemical Name: (2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-3-(S)-oxiranyl-2,3-dihydro-naphtho[1,2-b]furan
• CAS No.: 217486-38-9
• Molecular Formula: C₃₀H₃₆O₈
• Molecular Weight: 524.611
• Mol file: 217486-38-9.mol

Synonyms:(2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-3-(S)-oxiranyl-2,3-dihydro-naphtho[1,2-b]furan

Chemical Property of (2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-3-(S)-oxiranyl-2,3-dihydro-naphtho[1,2-b]furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-3-(S)-oxiranyl-2,3-dihydro-naphtho[1,2-b]furan

There total 12 articles about (2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-3-(S)-oxiranyl-2,3-dihydro-naphtho[1,2-b]furan 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: 3.0%

(S)-N,N-dimethyl-S-methyl-S-phenylsulfoximinuium tetrafluoroborate + (2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-carbaldehyde (217486-32-3) → (2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-3-(R)-oxiranyl-2,3-dihydro-naphtho[1,2-b]furan + (2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-3-(S)-oxiranyl-2,3-dihydro-naphtho[1,2-b]furan (217486-38-9)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; Ambient temperature; 1.) 40 min; 2.) 6 d;

DOI:10.1016/S0040-4039(97)00746-6

Reference yield:

(2R,3S)-9-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dimethoxy-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-4-ol → (2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-3-(S)-oxiranyl-2,3-dihydro-naphtho[1,2-b]furan (217486-38-9)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / 1,2-dimethoxy-ethane / -78 °C

2: 97 percent / CsF / dimethylformamide / 14 h / 120 °C

3: 90 percent / TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂; acetonitrile / 0.25 h / Ambient temperature

4: 1.) NaH / 1.) hexane, DMSO, RT, 40 min, 2.) hexane, DMSO, RT, 6 d

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; sodium hydride; cesium fluoride; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja982403t

Reference yield:

[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-methanol (217486-67-4) → (2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-3-(S)-oxiranyl-2,3-dihydro-naphtho[1,2-b]furan (217486-38-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / TPAP, NMO, 4 Angstroem molecular sieves / CH₂Cl₂; acetonitrile / 0.25 h / Ambient temperature

2: 1.) NaH / 1.) hexane, DMSO, RT, 40 min, 2.) hexane, DMSO, RT, 6 d

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; sodium hydride; In dichloromethane; acetonitrile;

DOI:10.1021/ja982403t

upstream raw materials:

methylenedimethyl sulfurane

(2R,3R)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-carbaldehyde

(dimethylamino)phenyloxosulfonium methylide

Diphenylsulfoniummethylid

Downstream raw materials:

(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-pent-3-en-1-ol

(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-3-(2,2-dimethyl-[1,3]dioxan-5-ylidene)-propan-1-ol

(Z)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol

(E)-(R)-1-[(2R,3S)-9-Benzyloxy-6,7-dimethoxy-4-(2-methoxy-ethoxymethoxy)-2,3,8-trimethyl-2,3-dihydro-naphtho[1,2-b]furan-3-yl]-4-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ol