Benzoic acid (2S,3S,4S,5R,6R)-4-benzyloxy-5-methoxy-2-pent-4-enyloxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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Chemical Name:Benzoic acid (2S,3S,4S,5R,6R)-4-benzyloxy-5-methoxy-2-pent-4-enyloxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester
CAS No.:187173-15-5
Molecular Formula:C₃₃H₃₈O₉S
Molecular Weight:610.725
Hs Code.:

Synonyms:Benzoic acid (2S,3S,4S,5R,6R)-4-benzyloxy-5-methoxy-2-pent-4-enyloxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2S,3S,4S,5R,6R)-4-benzyloxy-5-methoxy-2-pent-4-enyloxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2S,3S,4S,5R,6R)-4-benzyloxy-5-methoxy-2-pent-4-enyloxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

There total 7 articles about Benzoic acid (2S,3S,4S,5R,6R)-4-benzyloxy-5-methoxy-2-pent-4-enyloxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl 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: 100.0%

: 98-59-9
p-toluenesulfonyl chloride

: 187173-14-4
4-pentenyl 2-O-benzoyl-3-O-benzyl-4-O-methyl-α-D-mannopyranoside

: 187173-15-5
Benzoic acid (2S,3S,4S,5R,6R)-4-benzyloxy-5-methoxy-2-pent-4-enyloxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: With pyridine; for 7h; Ambient temperature;
DOI:10.1016/S0968-0896(96)00180-0

Reference yield:

: 125631-33-6,125647-51-0,132871-89-7,132871-95-5,132871-96-6,123487-65-0
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triol

: 187173-15-5
Benzoic acid (2S,3S,4S,5R,6R)-4-benzyloxy-5-methoxy-2-pent-4-enyloxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 46 percent / PPTS / dimethylformamide / 24 h

2: 1.) Bu₂SnO / 1.) MeOH, reflux, 3 h, 2.) DMF, 100 deg C, 20 min

3: 81 percent / pyridine / Ambient temperature

4: 85 percent / NaBH₃CN, mol. sieves 3A, TFA / dimethylformamide / 48 h / 0 - 20 °C

5: 90 percent / NaH / dimethylformamide / 3 h / -15 °C

6: 87 percent / DDQ / CH₂Cl₂; H₂O / 5 h / Ambient temperature

7: 100 percent / pyridine / 7 h / Ambient temperature

With pyridine; 3 A molecular sieve; pyridinium p-toluenesulfonate; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(96)00180-0

Reference yield:

: 4-pentenyl 4,6-O-(4-methoxybenzylidene)-α-D-mannopyranoside

: 187173-15-5
Benzoic acid (2S,3S,4S,5R,6R)-4-benzyloxy-5-methoxy-2-pent-4-enyloxy-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) Bu₂SnO / 1.) MeOH, reflux, 3 h, 2.) DMF, 100 deg C, 20 min

2: 81 percent / pyridine / Ambient temperature

3: 85 percent / NaBH₃CN, mol. sieves 3A, TFA / dimethylformamide / 48 h / 0 - 20 °C

4: 90 percent / NaH / dimethylformamide / 3 h / -15 °C

5: 87 percent / DDQ / CH₂Cl₂; H₂O / 5 h / Ambient temperature

6: 100 percent / pyridine / 7 h / Ambient temperature

With pyridine; 3 A molecular sieve; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(96)00180-0