4-O-acetyl-3,6-di-O-benzyl-5a-carba-1,2-di-O-(methylsulfonyl)-α-D-glucopyranose

Base Information

Chemical Name:4-O-acetyl-3,6-di-O-benzyl-5a-carba-1,2-di-O-(methylsulfonyl)-α-D-glucopyranose
CAS No.:142789-92-2
Molecular Formula:C₂₅H₃₂O₁₀S₂
Molecular Weight:556.655
Hs Code.:

Synonyms:4-O-acetyl-3,6-di-O-benzyl-5a-carba-1,2-di-O-(methylsulfonyl)-α-D-glucopyranose

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Chemical Property of 4-O-acetyl-3,6-di-O-benzyl-5a-carba-1,2-di-O-(methylsulfonyl)-α-D-glucopyranose

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Technology Process of 4-O-acetyl-3,6-di-O-benzyl-5a-carba-1,2-di-O-(methylsulfonyl)-α-D-glucopyranose

There total 7 articles about 4-O-acetyl-3,6-di-O-benzyl-5a-carba-1,2-di-O-(methylsulfonyl)-α-D-glucopyranose 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:

: 1125-88-8
benzaldehyde dimethyl acetal

: 142789-92-2
4-O-acetyl-3,6-di-O-benzyl-5a-carba-1,2-di-O-(methylsulfonyl)-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: p-TsOH / dimethylformamide / 2 h / 60 °C

2: 1) NaH / 1) DMF, r.t., 0.5 h, 2) DMF, r.t., 2 h

3: 1) NaCNBH₃, molecular sieves, HCl, 2) pyridine / 1) THF, ether, r.t., 2) r.t., overnight

4: 1) 4-methylmorpholine N-oxide, OsO₄, 2) NaHSO₃ / 1) acetone, H₂O, tBuOH, r.t., 2 h, 2) acetone, H₂O, tBuOH, 1 h

5: pyridine / 14 h / Ambient temperature

With pyridine; hydrogenchloride; osmium(VIII) oxide; molecular sieve; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; sodium hydrogensulfite; 4-methylmorpholine N-oxide; In N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)90491-9

Reference yield:

: 108867-01-2
(1S)-(-)-(1,3/2)-2,3-diacetoxy-4-cyclohexene-1-carboxylic acid

: 142789-92-2
4-O-acetyl-3,6-di-O-benzyl-5a-carba-1,2-di-O-(methylsulfonyl)-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

2: p-TsOH / dimethylformamide / 2 h / 60 °C

3: 1) NaH / 1) DMF, r.t., 0.5 h, 2) DMF, r.t., 2 h

4: 1) NaCNBH₃, molecular sieves, HCl, 2) pyridine / 1) THF, ether, r.t., 2) r.t., overnight

5: 1) 4-methylmorpholine N-oxide, OsO₄, 2) NaHSO₃ / 1) acetone, H₂O, tBuOH, r.t., 2 h, 2) acetone, H₂O, tBuOH, 1 h

6: pyridine / 14 h / Ambient temperature

With pyridine; hydrogenchloride; osmium(VIII) oxide; lithium aluminium tetrahydride; molecular sieve; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; sodium hydrogensulfite; 4-methylmorpholine N-oxide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)90491-9

Reference yield:

: 143058-81-5
(1R)-(1,3/2)-3-hydroxymethyl-5-cyclohexene-1,2-diol

: 142789-92-2
4-O-acetyl-3,6-di-O-benzyl-5a-carba-1,2-di-O-(methylsulfonyl)-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: p-TsOH / dimethylformamide / 2 h / 60 °C

2: 1) NaH / 1) DMF, r.t., 0.5 h, 2) DMF, r.t., 2 h

3: 1) NaCNBH₃, molecular sieves, HCl, 2) pyridine / 1) THF, ether, r.t., 2) r.t., overnight

4: 1) 4-methylmorpholine N-oxide, OsO₄, 2) NaHSO₃ / 1) acetone, H₂O, tBuOH, r.t., 2 h, 2) acetone, H₂O, tBuOH, 1 h

5: pyridine / 14 h / Ambient temperature

With pyridine; hydrogenchloride; osmium(VIII) oxide; molecular sieve; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; sodium hydrogensulfite; 4-methylmorpholine N-oxide; In N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)90491-9