(3aR,4R,6S,7aR)-4-[(R)-2-Hydroxy-1-(2-methoxy-ethoxymethoxy)-3-(toluene-4-sulfonyloxy)-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

Base Information

Chemical Name:(3aR,4R,6S,7aR)-4-[(R)-2-Hydroxy-1-(2-methoxy-ethoxymethoxy)-3-(toluene-4-sulfonyloxy)-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester
CAS No.:129907-96-6
Molecular Formula:C₂₄H₃₆O₁₂S
Molecular Weight:548.609
Hs Code.:

(3aR,4R,6S,7aR)-4-[(R)-2-Hydroxy-1-(2-methoxy-ethoxymethoxy)-3-(toluene-4-sulfonyloxy)-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

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Chemical Property of (3aR,4R,6S,7aR)-4-[(R)-2-Hydroxy-1-(2-methoxy-ethoxymethoxy)-3-(toluene-4-sulfonyloxy)-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

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Technology Process of (3aR,4R,6S,7aR)-4-[(R)-2-Hydroxy-1-(2-methoxy-ethoxymethoxy)-3-(toluene-4-sulfonyloxy)-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

There total 8 articles about (3aR,4R,6S,7aR)-4-[(R)-2-Hydroxy-1-(2-methoxy-ethoxymethoxy)-3-(toluene-4-sulfonyloxy)-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester 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:

: 129907-66-0
methyl 2,6-anhydro-8-O-benzoyl-3-deoxy-D-glycero-D-talo-octonate

: 129907-96-6,129907-97-7
(3aR,4R,6S,7aR)-4-[(R)-2-Hydroxy-1-(2-methoxy-ethoxymethoxy)-3-(toluene-4-sulfonyloxy)-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / Dowex 50W * 12(H+) resin / 2 h / Ambient temperature

2: 72 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 48 h / Ambient temperature

3: 72 percent / NaOMe / methanol / 17 h / Ambient temperature

4: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -60 deg C - -50 deg C, 15 min, 2) 10 min

5: 1) hexamethyldisilazane, 35percent KH, Me₂SO / 1) THF, 0 deg C, 1 h, 2a) -78 deg C, 1 h, 2b) r.t., overnight

6: 90 percent / N-methylmorpholine N-oxide monohydrate, water, 2.5percent OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h

7: 104 percent / pyridine / Ambient temperature

With pyridine; osmium(VIII) oxide; oxalyl dichloride; Dowex 50W * 12(H+) resin; water; sodium methylate; potassium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1016/0008-6215(90)84236-N

Reference yield:

: 129907-69-3
methyl 2,6-anhydro-3-deoxy-4,5-O-isopropylidene-7-O-(2-methoxyethoxymethyl)-D-glycero-D-talo-octonate

: 129907-96-6,129907-97-7
(3aR,4R,6S,7aR)-4-[(R)-2-Hydroxy-1-(2-methoxy-ethoxymethoxy)-3-(toluene-4-sulfonyloxy)-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -60 deg C - -50 deg C, 15 min, 2) 10 min

2: 1) hexamethyldisilazane, 35percent KH, Me₂SO / 1) THF, 0 deg C, 1 h, 2a) -78 deg C, 1 h, 2b) r.t., overnight

3: 90 percent / N-methylmorpholine N-oxide monohydrate, water, 2.5percent OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h

4: 104 percent / pyridine / Ambient temperature

With pyridine; osmium(VIII) oxide; oxalyl dichloride; water; potassium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1016/0008-6215(90)84236-N

Reference yield:

: 129907-84-2
methyl 2,6-anhydro-3,8,9-trideoxy-4,5-O-isopropylidene-7-O-(2-methoxyethoxymethyl)-D-glycero-D-talo-non-8-enonate

: 129907-96-6,129907-97-7
(3aR,4R,6S,7aR)-4-[(R)-2-Hydroxy-1-(2-methoxy-ethoxymethoxy)-3-(toluene-4-sulfonyloxy)-propyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / N-methylmorpholine N-oxide monohydrate, water, 2.5percent OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h

2: 104 percent / pyridine / Ambient temperature

With pyridine; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1016/0008-6215(90)84236-N